Ethanol → 3-Fluoro-5-(hydroxymethyl)benzonitrile
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([F:13])[CH:12]=1)[C:6](OC)=[O:7])#[N:2].C(O)C.[BH4-].[Li+]>O1CCCC1>[F:13][C:11]1[CH:12]=[C:3]([CH:4]=[C:5]([CH2:6][OH:7])[CH:10]=1)[C:1]#[N:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
(Step 2) To a mixed solution of methyl 3-cyano-5-fluorobenzoate (0.55 g) obtained in Step 1 in tetrahydrofuran:ethanol=10:1 (22 ml) was added lithium tetrahydroborate (0.10 g) at 0° C. After stirring at 55° C. for 1 hr, the reaction solution was quenched with ice and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 3-fluoro-5-(hydroxymethyl)benzonitrile (0.29 g).
Workup
- customthe reaction solution was quenched with ice
- extractionextracted with ethyl acetate
- washThe extract was washed with 1N hydrochloric acid
- dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-8bfef8f7a0554b469c0a79b4e87b200c
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08470859B2
Reaction notes
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