Acetone → 2-Fluoro-3-(hydroxymethyl)-6-iodobenzonitrile
Reaction equation
[F:1][C:2]1[C:9]([CH:10]=[O:11])=[CH:8][CH:7]=[C:6]([I:12])[C:3]=1[C:4]#[N:5].[BH4-].[Na+].CC(C)=O>CO>[F:1][C:2]1[C:9]([CH2:10][OH:11])=[CH:8][CH:7]=[C:6]([I:12])[C:3]=1[C:4]#[N:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of Example 220A (5.0 g, 18 mmol) in MeOH (100 mL) at 0° C. was treated with NaBH4 (822 mg, 22 mmol) and the mixture was stirred for 1 h at 0° C. Acetone was added and the mixture was stirred for 5 min, then concentrated to dryness. The residue was partitioned between H2O and EtOAc. The extracts were washed with brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography on silica gel, eluting with 3:2 hexanes/EtOAc to give the desired product (3.14 g). Rf=0.38 (3:2 hexane:EtOAc).
Workup
- stirringthe mixture was stirred for 5 min
- concentrationconcentrated to dryness
- customThe residue was partitioned between H2O and EtOAc
- washThe extracts were washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe residue was purified by flash chromatography on silica gel
- washeluting with 3:2 hexanes/EtOAc
Sources & evidence
- ORD record
- ord-186942ce403c40e491f3e82299385f69
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642776B2
Reaction notes
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