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inquiry4-(4-Fluorobenzoyl)-3-(hydroxymethyl)benzonitrile Application:80074892
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High purity Application:Pharmaceutical intermediates, Material synthesis and analyzing the expectant ingredients
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
4-flourophenylmagnesium bromide
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
Conditions | Yield |
---|---|
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile; 4-flourophenylmagnesium bromide In tetrahydrofuran; 1,2-dimethoxyethane at -10℃; for 3.5h; Stage #2: With water; ammonium chloride In tetrahydrofuran; 1,2-dimethoxyethane at 20℃; for 0.0833333h; | 86.2% |
In tetrahydrofuran at 0 - 5℃; for 5h; Solvent; Temperature; | 85% |
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile; 4-flourophenylmagnesium bromide In tetrahydrofuran; dichloromethane at -6 - -2℃; Stage #2: With water; ammonium chloride In tetrahydrofuran; dichloromethane | |
In tetrahydrofuran; toluene at -4 - -2℃; Product distribution / selectivity; |
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
1-Bromo-4-fluorobenzene
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
Conditions | Yield |
---|---|
Stage #1: 1-Bromo-4-fluorobenzene With magnesium In tetrahydrofuran Reflux; Inert atmosphere; Stage #2: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; | 63% |
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
4-flourophenylmagnesium bromide
A
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
B
4-(bis(4-fluorophenyl)hydroxymethyl)-3-(hydroxymethyl)benzonitrile
Conditions | Yield |
---|---|
In tetrahydrofuran; water at -10 - -5℃; for 3h; |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
dihydroxy-methyl-borane
(1S,2S)-N-Methylpseudoephedrine
Conditions | Yield |
---|---|
In toluene at 20 - 70℃; under 45.0045 - 52.5053 Torr; for 1.5h; Product distribution / selectivity; | 91% |
In toluene at 25 - 65℃; under 7.50075 - 82.5083 Torr; for 1 - 3h; Product distribution / selectivity; Molecular sieve; |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
tert-butyldimethylsilyl chloride
4-(4-fluorobenzoyl)-3-(tert-butyldimethylsiloxymethyl)benzonitrile
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 10 - 15℃; for 0.5h; | 84% |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
4-(bis(4-fluorophenyl)hydroxymethyl)-3-(hydroxymethyl)benzonitrile
4-[(4-fluoro-phenyl)-hydroxy-methyl]-3-hydroxymethyl-benzonitrile
Conditions | Yield |
---|---|
Stage #1: 4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile; 4-(bis(4-fluorophenyl)hydroxymethyl)-3-(hydroxymethyl)benzonitrile With sodium hydroxide; sodium tetrahydroborate In tetrahydrofuran; water at 0 - 15℃; for 0.5h; Stage #2: With phosphoric acid In water for 2h; Heating / reflux; |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
4-[(4-fluoro-phenyl)-hydroxy-methyl]-3-hydroxymethyl-benzonitrile
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol; toluene at 10 - 15℃; for 2h; |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 5 - 25℃; for 7 - 9h; |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
3-(N,N-dimethylamino)propylmagnesium chloride
4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile
Conditions | Yield |
---|---|
In tetrahydrofuran; 1,1-Dibromoethane; dichloromethane; toluene at -5 - 5℃; for 3 - 4h; |
Conditions | Yield |
---|---|
In toluene at 20 - 70℃; for 0.75h; Product distribution / selectivity; |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
(1S,2S)-N-Methylpseudoephedrine
diisopropoxymethylborane
B
isopropyl alcohol
Conditions | Yield |
---|---|
In toluene at 20 - 70℃; under 45.0045 - 52.5053 Torr; for 0.866667 - 1.03333h; Product distribution / selectivity; |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
(S)-1-dimethylamino-2-propanol
diisopropoxymethylborane
Conditions | Yield |
---|---|
In toluene at 20 - 45℃; for 0.75h; Product distribution / selectivity; |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
diisopropoxymethylborane
Conditions | Yield |
---|---|
In toluene at 20 - 70℃; for 0.75h; Product distribution / selectivity; |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
(1S,2R)-(+)-N-methylephedrine
diisopropoxymethylborane
Conditions | Yield |
---|---|
In toluene at 20 - 70℃; for 0.75h; Product distribution / selectivity; |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
(R)-2-dimethylamino-1-phenyl-ethanol
diisopropoxymethylborane
Conditions | Yield |
---|---|
In toluene at 20 - 70℃; for 0.75h; Product distribution / selectivity; |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
dihydroxy-methyl-borane
(1S,2R)-(+)-N-methylephedrine
Conditions | Yield |
---|---|
In toluene at 20 - 70℃; for 0.583333h; Product distribution / selectivity; |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
dihydroxy-methyl-borane
(S)-2-dimethylamino-1-phenylethanol
Conditions | Yield |
---|---|
In toluene at 50℃; under 45.0045 - 52.5053 Torr; Product distribution / selectivity; |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
Trimethylboroxine
(1S,2R)-(+)-N-methylephedrine
Conditions | Yield |
---|---|
In toluene at 20 - 70℃; for 0.583333h; Product distribution / selectivity; |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
3-(N,N-dimethylamino)propylmagnesium chloride
A
4-[(4-fluoro-phenyl)-hydroxy-methyl]-3-hydroxymethyl-benzonitrile
B
(S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)benzonitrile
Conditions | Yield |
---|---|
Stage #1: 4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile With (1S,2R)-(+)-N-methylephedrine In toluene at 20 - 70℃; for 0.75h; Stage #2: 3-(N,N-dimethylamino)propylmagnesium chloride In tetrahydrofuran; toluene at -80℃; for 0.2h; Product distribution / selectivity; | A n/a B n/a C n/a |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
3-(N,N-dimethylamino)propylmagnesium chloride
(S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)benzonitrile
Conditions | Yield |
---|---|
Stage #1: 4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile With dihydroxy-methyl-borane In toluene at 20 - 70℃; for 0.75h; Stage #2: 3-(N,N-dimethylamino)propylmagnesium chloride In tetrahydrofuran; toluene at -60℃; for 0.2h; Product distribution / selectivity; | n/a |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
3-(N,N-dimethylamino)propylmagnesium chloride
A
(S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)benzonitrile
Conditions | Yield |
---|---|
Stage #1: 4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile With (1S,2R)-(+)-N-methylephedrine In toluene at 20 - 70℃; for 0.75h; Stage #2: 3-(N,N-dimethylamino)propylmagnesium chloride In tetrahydrofuran; toluene at -80℃; for 0.2h; Product distribution / selectivity; | A n/a B n/a |
4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 1H-imidazole / dichloromethane / 0.5 h / 10 - 15 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 3.5 h / 5 - 60 °C / Inert atmosphere 2.2: 60 °C / Inert atmosphere View Scheme |
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