Sodium Bicarbonate → 2-Bromo-1-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)ethanone
Reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C:16](=[O:18])[CH3:17])[CH:9]=[CH:10][C:11]=2[O:12][CH:13]([F:15])[F:14])[CH2:3][CH2:2]1.[Br-:19].[Br-].[Br-].C[N+](C)(C)C1C=CC=CC=1.C[N+](C1C=CC=CC=1)(C)C.C[N+](C1C=CC=CC=1)(C)C.C(=O)([O-])O.[Na+]>C(O)(C)C>[Br:19][CH2:17][C:16]([C:8]1[CH:9]=[CH:10][C:11]([O:12][CH:13]([F:15])[F:14])=[C:6]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)[CH:7]=1)=[O:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To 250 ml of isopropanol solution containing 10.8 g (42.3 mmol) of 1-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)ethanone (see WO 9206963) was added 36.5 g (97.1 mmol) of trimethylphenylammonium tribromide at room temperature, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, a saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then, concentrated under reduced pressure to obtain 16.5 g of the title compound as a pale yellowish solid substantially quantitatively.
Workup
- customAfter completion of the reaction
- extractionthe mixture was extracted with ethyl acetate
- customThe organic layer after separation
- washwas washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-8bd1fb50a1c741bfa32fc0bf9f4a3006
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450319B2
Reaction notes
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