Boron trifluoride etherate → 2-Bromo-6H-dibenz[b,e]oxepin-11-one
Reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Br:14][C:15]1[CH:31]=[CH:30][C:18]([O:19][CH2:20][C:21]2[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=2[C:23]([OH:25])=O)=[CH:17][CH:16]=1.B(F)(F)F.CCOCC>ClCCl>[Br:14][C:15]1[CH:16]=[CH:17][C:18]2[O:19][CH2:20][C:21]3[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=3[C:23](=[O:25])[C:30]=2[CH:31]=1Participants
Procedure
Trifluoroacetic anhydride (56.0 mL, 400 mmol) was added dropwise to a dichloromethane (500 mL) solution of 2-(4-bromophenoxymethyl)benzoic acid (112 g, 364 mmol) at room temperature. The mixture was stirred at room temperature for 2 hour, BF3.OEt2 (10 mL, 169.3 mmol) was then added thereto, and the mixture was stirred at room temperature for additional 2 hours. The reaction mixture was washed with a saturated aqueous sodium bicarbonate solution, and then with a saturated sodium chloride solution, the washed mixture was then dried over anhydrous sodium sulfate, and the solvents were distilled off under a reduce pressure. The residue was purified by column chromatography (hexane-ethyl acetate=3:2), to give 96.0 g (91%) of the captioned compound in the form of crystals.
Workup
- stirringthe mixture was stirred at room temperature for additional 2 hours
- washThe reaction mixture was washed with a saturated aqueous sodium bicarbonate solution
- dry with materialwith a saturated sodium chloride solution, the washed mixture was then dried over anhydrous sodium sulfate
- distillationthe solvents were distilled off under a reduce pressure
- customThe residue was purified by column chromatography (hexane-ethyl acetate=3:2)
Sources & evidence
- ORD record
- ord-5f12d24f8ce84c31aa43db3ce0b61781
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222419B2
Reaction notes
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