Sodium borohydride → 4-Fluoro-6-trifluoromethyl-3H-isobenzofuran-1-one
Reaction equation
[F:1][C:2]1[C:3]([CH:21]=[O:22])=[C:4]([CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1)[C:5](N(C(C)C)C(C)C)=[O:6].[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:4]2[C:3]=1[CH2:21][O:22][C:5]2=[O:6]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
To a solution of 5.39 mmol 3-fluoro-2-formyl-N,N-diisopropyl-5-trifluoromethyl-benzamide in 17 ml ethanol was added portionwise 5.39 mmol sodium borohydride. The temperature was maintained at 30° C. with a water bath. The mixture was then stirred at room temperature for 50 minutes then cooled in an ice-water bath. Excess sodium borohydride was destroyed by adding HCl 2N. Ethanol was removed in vacuo. The residue was taken in 25 ml HCl 6N and refluxed at 120° C. for 2 hours. The mixture was cooled to room temperature and extracted 3 times with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a white solid (71% yield). MS (m/e): 220.2 (M+, 100%)
Workup
- temperaturethen cooled in an ice-water bath
- customExcess sodium borohydride was destroyed
- additionby adding HCl 2N
- customEthanol was removed in vacuo
- temperaturerefluxed at 120° C. for 2 hours
- temperatureThe mixture was cooled to room temperature
- extractionextracted 3 times with dichloromethane
- dry with materialThe combined organic phases were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)
Sources & evidence
- ORD record
- ord-e1fadac99d6d4afbb71e14770fbf6ad2
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557114B2
Reaction notes
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