Citric Acid → 2-Fluoro-4-(hydroxymethyl)benzonitrile
Reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[F:11])#[N:2].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CCO>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][C:4]=1[F:11])#[N:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 4-cyano-3-fluorobenzaldehyde, as described in Example 11, Step B, (620 mg, 4.16 mmol) in EtOH (30 mL) at 0° C. was added NaBH4 (157 mg, 4.16 mmol) in one portion. The reaction mixture was stirred at 0° C. for 10 min, then 10% aqueous citric acid (10 mL) was added and the solvent was removed under reduced pressure. The residue was partitioned between saturated aqueous NaHCO3 (10 nmL) and CH2Cl2 (30 mL). The aqueous layer was extracted further with CH2Cl2 (30 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo to provide the titled compound as a white solid.
Workup
- customthe solvent was removed under reduced pressure
- customThe residue was partitioned between saturated aqueous NaHCO3 (10 nmL) and CH2Cl2 (30 mL)
- extractionThe aqueous layer was extracted further with CH2Cl2 (30 mL)
- dry with materialThe combined organic extracts were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-ffbece1f146b4090be5e9ab25dae7144
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06441017B1
Reaction notes
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