Dimethyl Sulfide → 4-Bromo-2,6-difluorobenzyl alcohol
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[C:5]([C:6](O)=[O:7])=[C:4]([F:12])[CH:3]=1.CSC>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([F:12])[C:5]([CH2:6][OH:7])=[C:9]([F:11])[CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 4-bromo-2,6-difluorobenzoic acid (5 g, 21.10 mmol) in THF (100 mL) was added BH3.DMS (20.03 mL, 211 mmol) dropwise at rt. The resulting mixture was stirred at 60° C. for 16 h. After LCMS analysis showed the starting material had disappeared, the mixture was quenched by MeOH. The solvent was removed in vacuo to yield a white solid of (4-bromo-2,6-difluorophenyl)methanol (4.5 g, 20.02 mmol, 95.2% yield), which was used in the next step without further purification: ES-LCMS m/z 222.1 (M+1).
Workup
- customdropwise at rt
- customthe mixture was quenched by MeOH
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-16daa989498e4641b72c901c637150b4
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09035063B2
Reaction notes
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