Dimethyl Sulfide → 2-Fluoro-4-(2-hydroxyethyl)benzonitrile
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](O)=[O:11])=[CH:5][C:4]=1[F:13])#[N:2].S(C)C>C1COCC1>[F:13][C:4]1[CH:5]=[C:6]([CH2:9][CH2:10][OH:11])[CH:7]=[CH:8][C:3]=1[C:1]#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (4-cyano-3-fluorophenyl)acetic acid (25.6 g, 143 mmol) in 150 mL of dry THF was cooled by ice/water, and then BH3/Me2S (10 M, 15.7 mL, 157 mmol) was added slowly. The reaction was warmed to ambient temperature and stirred overnight. The mixture was quenched with MeOH and concentrated to dryness. The residue was partitioned between water and EtOAc. The organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to afford 2-fluoro-4-(2-hydroxyethyl)benzonitrile. 1H-NMR (400 MHz, CDCl3)
Workup
- customThe mixture was quenched with MeOH
- concentrationconcentrated to dryness
- customThe residue was partitioned between water and EtOAc
- washThe organic layers were washed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-784402fbef6e43aeb6ef0d3374632ac9
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018211B2
Reaction notes
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