Sodium borohydride → 2,5-Difluoro-4-(hydroxymethyl)benzonitrile
Reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH:10]=[O:11])[C:7]([F:12])=[CH:6][C:3]=1[C:4]#[N:5].[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:9]=[C:8]([CH2:10][OH:11])[C:7]([F:12])=[CH:6][C:3]=1[C:4]#[N:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 2.5 °C
Procedure
A solution of 2,5-difluoro-4-formylbenzonitrile (Preparation 20, 280 mg, 1.68 mmol) in ethanol (8 mL) was cooled to 0° C. in an ice/water bath. Sodium borohydride (63.4 mg, 1.68 mmol) was added and the reaction stirred at 0-5° C. for 5 hours. The mixture was quenched with aqueous hydrochloric acid (2 N, 20 mL) and extracted with EtOAc (25 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (25 mL), dried over sodium sulphate, and concentrated in vacuo to afford the title compound as a yellow oil, which crystallised on standing (182 mg, 64%).
Workup
- customThe mixture was quenched with aqueous hydrochloric acid (2 N, 20 mL)
- extractionextracted with EtOAc (25 mL)
- washThe organic layer was washed with saturated aqueous sodium bicarbonate (25 mL)
- dry with materialdried over sodium sulphate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-bacc506b8a654f068146a0d8c8ed40f4
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096500B2
Reaction notes
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