Lithium borohydride → (4-Bromo-3-(trifluoromethoxy)phenyl)methanol
Reaction equation
[BH4-].[Li+].[Br:3][C:4]1[CH:13]=[CH:12][C:7]([C:8](OC)=[O:9])=[CH:6][C:5]=1[O:14][C:15]([F:18])([F:17])[F:16]>C1COCC1>[Br:3][C:4]1[CH:13]=[CH:12][C:7]([CH2:8][OH:9])=[CH:6][C:5]=1[O:14][C:15]([F:16])([F:18])[F:17]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of lithium borohydride (1.16 g, 53.4 mmol) in THF (100 mL) was added methyl 4-bromo-3-(trifluoromethoxy)benzoate (10.6 g, 35.6 mmol) at 0° C., and the resulting solution was heated at 70° C. for 3 h under nitrogen atmosphere. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The combined organic layers were washed with saturated brine, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under vacuum to afford the crude title product (9.17 g, 34 mmol). MS (ESI) m/z 270.1 M+, 272.1 [M+2]+.
Workup
- customThe reaction was quenched with water
- extractionthe mixture was extracted with ethyl acetate
- washThe combined organic layers were washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- customThe filtrate was evaporated under vacuum
Sources & evidence
- ORD record
- ord-4038d9651be042f798ac1dea23501f5b
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156798B2
Reaction notes
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