Water → 3-Cyano-2,6-difluorobenzyl alcohol
Reaction equation
[F:1][C:2]1[C:9]([CH:10]=[O:11])=[C:8]([F:12])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[BH4-].[Na+].O>C(O)C>[F:1][C:2]1[C:9]([CH2:10][OH:11])=[C:8]([F:12])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A stirred solution of 300 mg (3.48 mmol) of 2,4-difluoro-3-formylbenzonitrile (CAS 149489-14-5) in 10 ml of ethanol at 0° C. was admixed with 34 mg (0.89 mmol) of sodium borohydride in portions. After stirring at 0° C. for 1 h, the reaction mixture was mixed with water and extracted three times with methyl tert-butyl ether. The combined organic extracts were washed with water and saturated aqueous sodium chloride solution, and dried with a phase separation cartridge. The solvent was drawn off to dryness under reduced pressure, which gave 280 mg (82% of theory) of the target compound.
Workup
- customat 0° C.
- extractionextracted three times with methyl tert-butyl ether
- washThe combined organic extracts were washed with water and saturated aqueous sodium chloride solution
- customdried with a phase separation cartridge
- customgave 280 mg (82% of theory) of the target compound
Sources & evidence
- ORD record
- ord-af5378c13d4a4c6cb95a22949e8ed655
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422285B2
Reaction notes
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