Boron trifluoride etherate → 1-[6-(5-Bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:26])=[C:6]([CH:25]=1)[C:7]([C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][CH2:15][N:14]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[C:13]=2[CH:24]=1)=O.B(F)(F)F.CCOCC.[SiH](CC)(CC)CC>ClCCCl.CC#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:26])=[C:6]([CH:25]=1)[CH2:7][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][CH2:15][N:14]([C:18](=[O:23])[C:19]([F:21])([F:22])[F:20])[C:13]=2[CH:24]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 1-[6-(5-bromo-2-chloro-benzoyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (36 g, 80.35 mmol) in 1,2-dichloroethane:MeCN 1:2 (180 mL) was added BF3.OEt2 (13.2 mL, 104 mmol) and Et3SiH (26.9 mL, 168.7 mmol) at 0° C. The reaction mixture was stirred overnight at room temperature then quenched by the addition of aq. NaHCO3 (˜200 mL). The resulting mixture was extracted with ethyl acetate (3×200 mL), and the combined organic layers were washed with brine (200 mL) and dried over sodium sulfate. Crude product obtained after evaporation of solvent was purified by silica gel column chromatography to furnish 1-[6-(5-bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (30 g).
Workup
- customthen quenched by the addition of aq. NaHCO3 (˜200 mL)
- extractionThe resulting mixture was extracted with ethyl acetate (3×200 mL)
- washthe combined organic layers were washed with brine (200 mL)
- dry with materialdried over sodium sulfate
- customCrude product obtained
- customafter evaporation of solvent
- customwas purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-cc9037bb3feb4687ac829379a822a059
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466114B2
Reaction notes
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