5111-65-9

Basic information

• Product Name: 2-Bromo-6-methoxynaphthalene
• Synonyms: BROMO(2-)-6-METHOXY NAPHTHALENE;BMN;2-BROMO-6-METHOXYNAPHTHALENE;2-BROMO-6-METHOXYNAPTHALENE;(6-BROM-2-NAPHTHYL)-METHYL ETHER;6-bromo-2-naphthyl methyl ether;6-BROMO-2-METHOXYNAPHTHALENE;6-METHOXY-2-BROMO NAPHTHALENE
• CAS NO: 5111-65-9
• Molecular Formula: C₁₁H₉BrO
• Molecular Weight: 237.09
• EINECS: 225-837-0
• Product Categories: Naphthalene derivatives;Ethers;Organic Building Blocks;Oxygen Compounds;Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;C11 to C12;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Aromatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 5111-65-9.mol
• Article Data: 35

Chemical Properties

• Melting Point: 106-109 °C(lit.)
• Boiling Point: 160-164°C 3mm
• Flash Point: 160-164°C/3mm
• Appearance: White to light beige/Powder
• Density: 1.4105 (rough estimate)
• Vapor Pressure: 0.000459mmHg at 25°C
• Refractive Index: 1.5290 (estimate)
• Storage Temp.: Room temperature.
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• Water Solubility: Soluble in DMSO. Insoluble in water.
• BRN: 2043874
• CAS DataBase Reference: 2-Bromo-6-methoxynaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-6-methoxynaphthalene(5111-65-9)
• EPA Substance Registry System: 2-Bromo-6-methoxynaphthalene(5111-65-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 5111-65-9(Hazardous Substances Data)

Usage

Description

2-Bromo-6-methoxynaphthalene is an organic compound characterized by its white to light beige powder form. It is a derivative of naphthalene, with a bromine atom at the 2nd position and a methoxy group at the 6th position. 2-Bromo-6-methoxynaphthalene is known for its chemical properties and is utilized in various applications across different industries.

Uses

Used in Pharmaceutical Industry:
2-Bromo-6-methoxynaphthalene is used as an intermediate in the synthesis of nabumetone [4-(6-methoxy-2-naphthalenyl)-2-butanone], a nonsteroidal anti-inflammatory drug (NSAID). The Heck reaction is employed in this synthesis process, which is significant for the development of medications aimed at reducing inflammation and pain.
Used in Chemical Synthesis:
2-Bromo-6-methoxynaphthalene serves as a key building block in the creation of various organic compounds due to its unique structure. Its bromine atom and methoxy group make it a versatile compound for use in chemical synthesis, allowing for the development of new molecules with potential applications in various fields, such as materials science, pharmaceuticals, and agrochemicals.

InChI:InChI=1/C11H9BrO/c1-13-11-5-3-8-6-10(12)4-2-9(8)7-11/h2-7H,1H3

Synthetic route

6-bromo-naphthalen-2-ol (15231-91-1) + methyl bromide (74-83-9) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
With potassium carbonate In acetonitrile for 3h; Reflux;	99%
With potassium tert-butylate In dimethyl sulfoxide for 0.25h;

2-Methoxynaphthalene (93-04-9) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
With hydrogen bromide; sodium bromide In chloroform; water at 0℃; Electrochemical reaction;	98%
With bromine; acetic acid at 55 - 85℃; under 760.051 Torr; for 0.275h; Temperature;	90.2%
With tin; bromine; acetic acid 2.) reflux; Multistep reaction;

6-bromo-naphthalen-2-ol (15231-91-1) + methyl iodide (74-88-4) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃;	97%
With caesium carbonate In acetone at 0 - 26℃;	97%
With potassium carbonate In N,N-dimethyl-formamide	96%

6-bromo-naphthalen-2-ol (15231-91-1) + carbonic acid dimethyl ester (616-38-6) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
Stage #1: 6-bromo-naphthalen-2-ol With tetrabutyl-ammonium chloride; potassium carbonate at 135℃; Neat (no solvent); Stage #2: carbonic acid dimethyl ester at 130 - 135℃; for 6h; Neat (no solvent);	95%

6-bromo-naphthalen-2-ol (15231-91-1) + dimethyl sulfate (77-78-1) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	92%
With caesium carbonate In acetone at 20℃; for 0.5h;	91%
With aluminum oxide; potassium hydroxide for 6h; microwave irradiation;	88%

6-bromo-naphthalen-2-ol (15231-91-1) + tetramethlyammonium chloride (75-57-0) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
With caesium carbonate In 1,2-dimethoxyethane at 145℃; for 1h; Microwave irradiation; Inert atmosphere; Sealed vessel;	92%

6-bromo-naphthalen-2-ol (15231-91-1) + methyl halide → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;	81%
With potassium carbonate In N,N-dimethyl-formamide at 80℃;

6-bromo-naphthalen-2-ol (15231-91-1) + 4-benzyl-4-methylmorpholinium chloride (55476-88-5) → 2-Bromo-6-methoxynaphthalene (5111-65-9) + 6-benzyloxy-2-bromonaphthalene (2234-45-9)

Conditions	Yield
With potassium carbonate at 150 - 160℃; for 2h;	A n/a B 72%

6-bromonaphthalen-2-yl 4-methylbenzenesulfonate + potassium methanolate (865-33-8) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
In acetonitrile at 45℃; Schlenk technique; Inert atmosphere;	70%
In acetonitrile at 45℃; for 18.5h;	70%

2-methoxy-6-(prop-1-en-2-yl)-naphthalene (34352-92-6) → 2-Bromo-6-methoxynaphthalene (5111-65-9) + 2-(2-Bromo-1-fluoro-1-methyl-ethyl)-6-methoxy-naphthalene (182816-10-0) + 1-Bromo-6-(2-bromo-1-fluoro-1-methyl-ethyl)-2-methoxy-naphthalene

Conditions	Yield
With N-Bromosuccinimide; triethylamine tris(hydrogen fluoride) In dichloromethane for 14h; Ambient temperature;	A 4% B 29% C 67%

potassium trifluoro(6-methoxynaphthalen-2-yl)borate (1163708-25-5, 1412414-27-7) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
With acetic acid; lithium bromide In dimethyl sulfoxide at 100℃; for 8h; Schlenk technique;	56%

methanol (67-56-1) + 6-bromo-naphthalen-2-ol (15231-91-1) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
With toluene-4-sulfonic acid at 100℃;
With sulfuric acid
at 100℃;

6-bromo-2-methoxy-1-naphthoic acid (610277-16-2) → 6-bromo-naphthalen-2-ol (15231-91-1) + 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
With quinoline; copper

C15H19N3O → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
With molecular sieve; Amberlyst XN-1010 resin; potassium iodide In N,N-dimethyl-formamide; acetonitrile at 70℃;

6-methoxy-2-naphthylamine (13101-88-7) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) aq. HCl, NaNO2, 2) K2CO3 / 1) H2O, 0 deg C, 1 h, 2) H2O 2: KI, Amberlyst XN-1010 resin, ground molecular sieve / acetonitrile; dimethylformamide / 70 °C View Scheme

2-methoxy-1-naphthaldehyde (5392-12-1) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium permanganate; potassium carbonate; aqueous acetone 2: diethyl ether 3: acetic acid; bromine / Irradiation.Sonnenlicht 4: ethanolic NaOH-solution 5: copper-powder; quinoline View Scheme

1-bromo-2-naphthol (573-97-7) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: tin; hydrochloric acid; alcohol 2: glacial acetic acid; bromine 3: tin (II)-chloride; concentrated hydrochloric acid; alcohol 4: KOH-solution View Scheme
Multi-step reaction with 4 steps 1: tin; hydrochloric acid; alcohol 2: glacial acetic acid; bromine 3: sodium amalgam; alcohol 4: KOH-solution View Scheme
Multi-step reaction with 5 steps 1: tin; hydrochloric acid; alcohol 2: glacial acetic acid; bromine 3: tin (II)-chloride; concentrated hydrochloric acid / weit. Reagens: Alkohol 4: sodium amalgam; alcohol 5: KOH-solution View Scheme
Multi-step reaction with 4 steps 1: tin; hydrochloric acid; alcohol 2: glacial acetic acid; bromine 3: sodium amalgam; alcohol 4: KOH-solution View Scheme

1,6-dibromo-2-naphthol (16239-18-2) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: tin (II)-chloride; concentrated hydrochloric acid; alcohol 2: KOH-solution View Scheme
Multi-step reaction with 2 steps 1: tin; concentrated hydrochloric acid; alcohol 2: KOH-solution View Scheme
Multi-step reaction with 2 steps 1: acetic acid; tin / 3 h / 100 - 120 °C 2: potassium carbonate / acetone; water / 4 h / 10 - 50 °C / Cooling View Scheme

2-methoxy-1-naphthoic acid (947-62-6) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: diethyl ether 2: acetic acid; bromine / Irradiation.Sonnenlicht 3: ethanolic NaOH-solution 4: copper-powder; quinoline View Scheme

methyl ester of 2-methoxy-1-naphthalenecarboxylic acid (13343-92-5) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; bromine / Irradiation.Sonnenlicht 2: ethanolic NaOH-solution 3: copper-powder; quinoline View Scheme

4,6-dibromo-β-naphthol (102153-54-8) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium amalgam; alcohol 2: KOH-solution View Scheme

1,4,6-tribromo-[2]naphthol (116632-10-1) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium amalgam; alcohol 2: KOH-solution View Scheme
Multi-step reaction with 3 steps 1: tin (II)-chloride; concentrated hydrochloric acid / weit. Reagens: Alkohol 2: sodium amalgam; alcohol 3: KOH-solution View Scheme

1,3,4,6-tetrabromo-[2]naphthol (98994-65-1) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium amalgam; alcohol 2: KOH-solution View Scheme

methyl 6-bromo-2-methoxy-1-naphthoate (854817-26-8) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanolic NaOH-solution 2: copper-powder; quinoline View Scheme

β-naphthol (135-19-3) → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: glacial acetic acid; bromine 2: tin (II)-chloride; concentrated hydrochloric acid; alcohol 3: KOH-solution View Scheme
Multi-step reaction with 3 steps 1: glacial acetic acid; bromine 2: sodium amalgam; alcohol 3: KOH-solution View Scheme
Multi-step reaction with 4 steps 1: glacial acetic acid; bromine 2: tin (II)-chloride; concentrated hydrochloric acid / weit. Reagens: Alkohol 3: sodium amalgam; alcohol 4: KOH-solution View Scheme

2-(6-methoxynaphthyl)magnesium bromide + methylmagnesium chloride (676-58-4) → 2-Bromo-6-methoxynaphthalene (5111-65-9) + naproxen (23981-80-8)

Conditions	Yield
In tetrahydrofuran

6-bromo-naphthalen-2-ol (15231-91-1) + kieselguhr → 2-Bromo-6-methoxynaphthalene (5111-65-9)

Conditions	Yield
With sodium hydroxide; dimethyl sulfate In water

2-Bromo-6-methoxynaphthalene (5111-65-9) + 2-methyl-but-3-yn-2-ol (115-19-5) → 2-methyl-4-(6-methoxynaphthalen-2-yl)but-3-yn-2-ol (129112-99-8)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine for 17h; Heating;	100%
With copper(l) iodide; ethanolamine; triphenylphosphine; palladium on activated charcoal In water; acetonitrile at 80℃; for 15h; Sonogashira cross-coupling;	80%
With bis-triphenylphosphine-palladium(II) chloride; copper(I) In triethylamine at 90℃; for 20h;	79%
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine; lithium bromide; copper(ll) bromide In tetrahydrofuran at 90℃; for 2h; Substitution; Title compound not separated from byproducts;
With copper(l) iodide; palladium diacetate; N-ethyl-N,N-diisopropylamine; triphenylphosphine In N,N-dimethyl-formamide at 70℃; for 12h; Inert atmosphere; Glovebox;

2-Bromo-6-methoxynaphthalene (5111-65-9) + phenylboronic acid (98-80-6) → 2-methoxy-6-phenylnaphthalene (59115-43-4)

Conditions	Yield
With potassium phosphate; (η5-C5H5)Re(NO)(P(C6H5)3)P(C6H5)2; palladium diacetate In toluene at 100℃; for 0.25h; Suzuki cross-couplings reaction;	100%
With palladium diacetate; tetrabutylammomium bromide; potassium carbonate In water at 70℃; for 1h;	99%
With potassium fluoride; o-(dicyclohexylphosphino)diisopropylbenzamide; tris(dibenzylideneacetone)dipalladium (0) In N,N-dimethyl-formamide at 80℃; for 40h; Suzuki cross-coupling;	98%

2-Bromo-6-methoxynaphthalene (5111-65-9) + copper(I) cyanide (544-92-3) → 2-cyano-6-methoxynaphthalene (67886-70-8)

Conditions	Yield
In N,N-dimethyl-formamide for 4h; Heating;	100%
Substitution;

2-Bromo-6-methoxynaphthalene (5111-65-9) → (6-methoxy-2-naphthalene)boronic acid (156641-98-4)

Conditions	Yield
Stage #1: 2-Bromo-6-methoxynaphthalene With sec.-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane Stage #3: With hydrogenchloride In tetrahydrofuran; hexane for 0.166667h;	100%
Stage #1: 2-Bromo-6-methoxynaphthalene With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: With Trimethyl borate In tetrahydrofuran	89%
Stage #1: 2-Bromo-6-methoxynaphthalene With magnesium In tetrahydrofuran Stage #2: With Trimethyl borate In tetrahydrofuran at 0 - 5℃; for 0.25h; Stage #3: With water In tetrahydrofuran for 0.25h;	80%
Stage #1: 2-Bromo-6-methoxynaphthalene With n-butyllithium In tetrahydrofuran; hexane at -60℃; for 1.16667h; Stage #2: With boric acid tributyl ester In tetrahydrofuran; hexane at -60 - 5℃; for 2.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at 5℃;	59%
Stage #1: 2-Bromo-6-methoxynaphthalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78 - 0℃; for 1.16667h;

2-Bromo-6-methoxynaphthalene (5111-65-9) → 6-bromo-naphthalen-2-ol (15231-91-1)

Conditions	Yield
With boron tribromide In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;	100%
With hydrogen bromide; 1-butyl-3-methylimidazolium Tetrafluoroborate at 115℃; for 10h;	95%
With boron tribromide In dichloromethane at 0 - 20℃; for 1h;	75%

2-Bromo-6-methoxynaphthalene (5111-65-9) → 1,6-dibromo-2-methoxynaphthalene (66996-59-6)

Conditions	Yield
With N-bromosuccimimide In tetrahydrofuran for 2h; Heating;	100%
With N-Bromosuccinimide In tetrahydrofuran for 2h; Reflux;	100%
With N-Bromosuccinimide In tetrahydrofuran for 2h; Reflux;	97%

carbon monoxide (201230-82-2) + 2-Bromo-6-methoxynaphthalene (5111-65-9) → 2-methoxy-6-naphthoic acid (2471-70-7)

Conditions	Yield
With dicobalt octacarbonyl; potassium carbonate; methyloxirane In methanol at 60℃; under 760 Torr; for 10.5h;	100%

Dichloromethyl methyl ether (4885-02-3) + 2-Bromo-6-methoxynaphthalene (5111-65-9) → 6-bromo-2-methoxynaphthalene-1-carbaldehyde (247174-18-1)

Conditions	Yield
With titanium tetrachloride In dichloromethane at 40℃; for 2h;	100%
With titanium tetrachloride In dichloromethane at 0 - 20℃;	100%
With titanium tetrachloride In dichloromethane at 0 - 20℃;	100%

styrene (100-42-5) + 2-Bromo-6-methoxynaphthalene (5111-65-9) → (E)-2-methoxy-6-styrylnaphthalene (123871-53-4)

Conditions	Yield
With tetrabutylammomium bromide; caesium carbonate; palladium(II) acetylacetonate In N,N-dimethyl acetamide at 100℃; for 3h; Heck reaction;	99%
With C38H38Cl2N4P2Pd; sodium carbonate In N,N-dimethyl-formamide at 140℃; for 3h; Reagent/catalyst; Heck Reaction; Inert atmosphere;	87%
With C11H20N3(1+)*C2F6NO4S2(1-); palladium diacetate at 70℃; for 6h; Heck Reaction; Ionic liquid; Inert atmosphere;	75%
With sodium acetate; palladium In N,N-dimethyl acetamide at 130 - 140℃;	60%

methyl 2-methylbutanoate (868-57-5) + 2-Bromo-6-methoxynaphthalene (5111-65-9) → methyl α-(6-methoxy-naphthalen-2-yl)-α-methyl-butyrate

Conditions	Yield
With tri-tert-butyl phosphine; lithium dicyclohexylamide; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 10h;	99%

4,4-dimethylcyclohexenone (1073-13-8) + 2-Bromo-6-methoxynaphthalene (5111-65-9) → 2-(4,4-dimethylcyclohexa-1,5-dienyl)-6-methoxynaphthalene

Conditions	Yield
Stage #1: 4,4-dimethylcyclohexenone With tris-(dibenzylideneacetone)dipalladium(0); toluene-4-sulfonic acid hydrazide; lithium tert-butoxide; XPhos In 1,4-dioxane for 0.0166667h; Inert atmosphere; Stage #2: 2-Bromo-6-methoxynaphthalene In 1,4-dioxane at 110℃; Inert atmosphere;	99%

ethyl bromide (74-96-4) + 2-Bromo-6-methoxynaphthalene (5111-65-9) → 2-methoxy-6-ethylnaphthalene (21388-17-0)

Conditions	Yield
Stage #1: ethyl bromide With magnesium In tetrahydrofuran for 0.666667h; Inert atmosphere; Stage #2: 2-Bromo-6-methoxynaphthalene With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran at 60℃; for 3h; Inert atmosphere;	99%

2-Bromo-6-methoxynaphthalene (5111-65-9) + lithium methyltriolborate → 2-methyl-6-methoxynaphthalene (26386-94-7)

Conditions	Yield
With palladium diacetate; ruphos In methanol; water at 80℃; for 12h; Inert atmosphere;	99%

1-decyne (764-93-2) + 2-Bromo-6-methoxynaphthalene (5111-65-9) → C27H30O

Conditions	Yield
With water; potassium carbonate In 1-methyl-pyrrolidin-2-one at 135℃; for 24h; Catalytic behavior; Sonogashira Cross-Coupling;	99%

n-butyl magnesium bromide (693-03-8) + 2-Bromo-6-methoxynaphthalene (5111-65-9) → 2-butyl-6-methoxynaphthalene (701270-26-0)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran at 0℃; for 4h; Reflux; Inert atmosphere;	99%

9-fluorenone (486-25-9) + 2-Bromo-6-methoxynaphthalene (5111-65-9) → 9-(6-methoxynaphthalene-2-yl)-9H-fluorene-9-ol

Conditions	Yield
Stage #1: 2-Bromo-6-methoxynaphthalene With iodine; magnesium In tetrahydrofuran Inert atmosphere; Stage #2: 9-fluorenone In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;	99%

2-Bromo-6-methoxynaphthalene (5111-65-9) + (1-morpholino-1-oxopropan-2-yl)zinc pivalate → 2-(6-methoxynaphthalen-2-yl)-1-morpholinopropan-1-one

Conditions	Yield
With bis(dibenzylideneacetone)-palladium(0); DavePhos In tetrahydrofuran at 40℃; for 4h; Negishi Coupling; Inert atmosphere;	99%

2-Bromo-6-methoxynaphthalene (5111-65-9) + allyltributylstanane (24850-33-7) → 2-methoxy-6-(2'-propenyl)naphthalene (139633-65-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); lithium chloride In N,N-dimethyl-formamide at 100℃; for 5h; Inert atmosphere;	99%

2-Bromo-6-methoxynaphthalene (5111-65-9) → C11H8(2)HBrO

Conditions	Yield
With tetrakis(tetrabutylammonium)decatungstate(VI); 2,4,6-Triisopropylthiophenol; water-d2 In acetonitrile for 48h; Irradiation;	99%

2-Bromo-6-methoxynaphthalene (5111-65-9) + trimethylsilylacetylene (1066-54-2) → ((6-methoxynaphthalen-2-yl)ethynyl)trimethylsilane (454431-03-9)

Conditions	Yield
Stage #1: trimethylsilylacetylene With ethylmagnesium bromide In tetrahydrofuran Heating; Stage #2: 2-Bromo-6-methoxynaphthalene With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; benzene Heating;	98%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine In tetrahydrofuran at 78℃; for 20h; Inert atmosphere;	98.4%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine; triphenylphosphine In tetrahydrofuran at 20℃; for 15h;	92%

2-Bromo-6-methoxynaphthalene (5111-65-9) → (±)-6,6′-dibromo-2,2′-dimethoxy-1,1′-binaphthalene (74866-27-6, 117745-41-2, 117745-45-6)

Conditions	Yield
With boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at -40℃; for 1.5h;	98%
With boron trifluoride diethyl etherate; thallium(III) trifluoroacetate In acetonitrile Ambient temperature;	76%

Benzophenone imine (1013-88-3) + 2-Bromo-6-methoxynaphthalene (5111-65-9) → N-(diphenyl methylene)-6-methoxy-2-naphthylamine

Conditions	Yield
With potassium tert-butylate; bis(dibenzylideneacetone)-palladium(0); 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 100℃; for 5h;	98%

2-Bromo-6-methoxynaphthalene (5111-65-9) + K4[Fe(CN)6] → 2-cyano-6-methoxynaphthalene (67886-70-8)

Conditions	Yield
With sodium carbonate; palladium diacetate at 140℃; for 16h;	98%
With sodium carbonate; potassium iodide; N,N`-dimethylethylenediamine; copper(II) bis(tetrafluoroborate) In N,N-dimethyl acetamide at 140℃; for 16h;	96%

2-Bromo-6-methoxynaphthalene (5111-65-9) + oxalic acid diethyl ester (95-92-1) → ethyl 2-(6-methoxynaphthalen-2-yl)-2-oxoacetate (56547-13-8)

Conditions	Yield
Stage #1: 2-Bromo-6-methoxynaphthalene With magnesium In tetrahydrofuran at 20℃; for 0.5h; Stage #2: oxalic acid diethyl ester In tetrahydrofuran at -78 - 0℃; for 5h;	98%
Stage #1: 2-Bromo-6-methoxynaphthalene With n-butyllithium In tetrahydrofuran at -80℃; for 3h; Stage #2: oxalic acid diethyl ester In tetrahydrofuran at -80℃; for 5h;	81%
Stage #1: 2-Bromo-6-methoxynaphthalene With iodine; magnesium In tetrahydrofuran Inert atmosphere; Stage #2: oxalic acid diethyl ester In tetrahydrofuran at -78 - 20℃; for 14h; Inert atmosphere;
Stage #1: 2-Bromo-6-methoxynaphthalene With iodine; magnesium In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; Stage #2: oxalic acid diethyl ester In tetrahydrofuran at -78 - 20℃; Inert atmosphere;

2-trimethylsilylpropionitrile (18151-58-1) + 2-Bromo-6-methoxynaphthalene (5111-65-9) → 2-(6-methoxynaphthalen-2-yl)propionitrile (86603-94-3)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); zinc(II) fluoride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 90℃; for 18h;	98%

2-Bromo-6-methoxynaphthalene (5111-65-9) → 2-Methoxynaphthalene (93-04-9)

Conditions	Yield
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 3h;	98%
With hydrogen; triethylamine In methanol; water at 120℃; under 22502.3 Torr; for 96h; Autoclave;	95%
With sodium hydride; lithium iodide In tetrahydrofuran; mineral oil at 50℃; for 7h; Reagent/catalyst; Solvent; Temperature; Sealed tube;	81%

Dimethyldisulphide (624-92-0) + 2-Bromo-6-methoxynaphthalene (5111-65-9) → (6-methoxynaphthalen-2-yl)(methyl)sulfane (210823-16-8)

Conditions	Yield
Stage #1: 2-Bromo-6-methoxynaphthalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: Dimethyldisulphide In tetrahydrofuran; hexane at 20℃; for 1h; Inert atmosphere;	98%
Stage #1: 2-Bromo-6-methoxynaphthalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: Dimethyldisulphide In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere; Stage #3: With ammonium hydroxide In tetrahydrofuran; hexane at 20℃; Inert atmosphere;	98%
Stage #1: 2-Bromo-6-methoxynaphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: Dimethyldisulphide In tetrahydrofuran at 20℃; for 1h;	90.2%
With sodium hydroxide; n-butyllithium In tetrahydrofuran	58%

1-ethynyl-2-methoxybenzene (767-91-9) + 2-Bromo-6-methoxynaphthalene (5111-65-9) → 2-methoxy-6-((2-methoxyphenyl)ethynyl)naphthalene (1048030-55-2)

Conditions	Yield
With copper(l) iodide; potassium tetrachloropalladate(II); N,N,N,N,-tetramethylethylenediamine; di‐tert‐butyl‐(1‐phenylindol‐2‐yl)phosphane at 80℃; for 20h; Sonogashira coupling; Inert atmosphere;	98%

Upstream product

• 67-56-1 methanol 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 610277-16-2 6-bromo-2-methoxy-1-naphthoic acid 
• 77-78-1 dimethyl sulfate 
• 74-83-9 methyl bromide 
• 93-04-9 2-Methoxynaphthalene 
• 74-88-4 methyl iodide 
• 34352-92-6 2-methoxy-6-(prop-1-en-2-yl)-naphthalene 
• 13101-88-7 6-methoxy-2-naphthylamine 
• 5392-12-1 2-methoxy-1-naphthaldehyde 
• 573-97-7 1-bromo-2-naphthol 
• 16239-18-2 1,6-dibromo-2-naphthol 
• 947-62-6 2-methoxy-1-naphthoic acid 
• 13343-92-5 methyl ester of 2-methoxy-1-naphthalenecarboxylic acid 

Downstream Products

• 92643-16-8 6-Bromo-1-(chloromethyl)-2-methoxynaphthalene 
• 18410-39-4 (6-methoxynaphthalen-2-yl)trimethylsilane 
• 18768-68-8 (6-methoxy-[2]naphthyl)-triphenyl-silane 
• 13101-88-7 6-methoxy-2-naphthylamine 
• 247174-18-1 6-bromo-2-methoxynaphthalene-1-carbaldehyde 
• 32725-05-6 2-<1-hydroxyethyl>-6-methoxynaphthalene 
• 115378-00-2 [2-(6-Methoxy-naphthalen-2-yl)-phenyl]-carbamic acid tert-butyl ester 
• 71964-75-5 2-(6-methoxy-2-naphthoyl)benzoic acid 
• 42924-53-8 nabumetone 
• 127053-21-8 4-(6-methoxy-2-naphthyl)-3-butene-2-ol 
• 2471-70-7 2-methoxy-6-naphthoic acid 
• 29619-45-2 6,6'-dimethoxy-2,2'-binaphthalene 
• 80493-89-6 2-(4'-cyanophenyl)-6-methoxynaphthalene 
• 103710-47-0 N,N-Diisopropyl-2-(6-methoxy-naphthalen-2-yl)-benzamide 

Relevant articles and documents

A practical synthesis of 2-bromo-6-methoxynaphthalene

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The intramolecular Schmidt reaction of azides with tertiary alcohols: Synthesis of 5-(α-naphthyl)- and 5-(β-naphthyl)indolizidines as potential dopamine analogs and non-opiate antinociceptive agents

Intramolecular Schmidt reaction of the azido alcohols 9, 11, and 12 afforded the 5-naphthylindolizidines 10, 13, and 14, respectively. The naphthylmethylamine subunit present in each has an amine and a π-system oriented in a fashion similar to the β-phenethylamine subunit of dopamine and many of its agonists and antagonists. These analogs also closely resemble the bicyclic tertiary amines 8, which have recently been found to exhibit non-opiate analgesic activity. Testing of 10, 13, and 14 for dopaminergic activity is described.

Preparation method of nitrogen-alkyl (deuterated alkyl) aromatic heterocycle and alkyl (deuterated alkyl) aryl ether compound

The invention provides a method for preparing nitrogen-alkyl(deuterated alkyl)aromatic heterocycle and alkyl(deuterated alkyl)aryl ether compounds. The method adopted in the invention specifically comprises the following steps: firstly, adding an alkoxy base (MOR') or a combination reagent Q (comprising a base M'X, an alcohol C and a molecular sieve E) into a solvent B to be stirred; then, addingan aromatic compound D of nitrogen sulfonyl or oxygen sulfonyl into a mixture; separating and purifying after reaction to obtain nitrogen-alkyl(deuterated alkyl)aromatic heterocycle or alkyl(deuterated alkyl)aryl ether. The method can realize one-step conversion from an electron withdrawing benzenesulfonyl protecting group on a nitrogen or oxygen atom to an electron donating alkyl protecting group, avoids using highly toxic alkyl halide, and has advantages of being efficient, economical, environmentally friendly, mild in condition, good in substrate universality and high in yield; the prepareddeuterated compounds can be widely applied to the fields of pharmaceutical chemistry and organic chemistry synthesis.

Detosylative (Deutero)alkylation of Indoles and Phenols with (Deutero)alkoxides

An efficient strategy for N/O-(deutero)alkylation of indoles and phenols with alkoxides/alcohols as the alkylation reagents is described. The consecutive detosylation/alkylation transformations feature mild reaction conditions, high ipso-selectivity, and good functional group tolerance (>50 examples). A one-pot selective N-alkylation of unprotected indoles with alcohols and TsCl is also realized. The application of this method is demonstrated by the introduction of isotope-labeled (CD3 and 13CH3) groups using the readily accessible labeled alcohols and the synthesis of pharmaceuticals.