Benzoyl Peroxide → Ethyl 4-(bromomethyl)-3-(trifluoromethyl)benzoate
Reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:27][C:28]1[CH:38]=[CH:37][C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:30][C:29]=1[C:39]([F:42])([F:41])[F:40]>C(Cl)(Cl)(Cl)Cl.ClCCl>[Br:1][CH2:27][C:28]1[CH:38]=[CH:37][C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:30][C:29]=1[C:39]([F:41])([F:40])[F:42]Participants
Procedure
N-Bromosuccinimide (1.04 g, 5.83 mmol) and benzoyl peroxide (0.12 g, 0.49 mmol) were added to a solution of ethyl 4-methyl-3-(trifluoromethyl)benzoate (1.06 g, 4.56 mmol) in carbon tetrachloride (25 mL). The reaction mixture was heated at reflux overnight. After it was cooled to room temperature, it was diluted with dichloromethane (50 mL), and washed with water (20 mL). The aqueous layer was extracted with dichloromethane (20 mL). It was dried over Na2SO4 and concentrated. It was purified by prep-TLC (Hexanes:ethyl acetate=10:1) to give the product as an oil (0.60 g, 44%) 1H NMR (400 MHz, DMSO-d6) δ 8.31 (d, J=1.6 Hz, 1H), 8.20 (dd, J=4.8, 1.6 Hz, 1H), 7.68 (d, J=8.0 Hz, 1H), 4.64 (s, 1H), 4.40 (q, J=7.2 Hz, 2H), 1.40 (t, J=7.2 Hz, 3H).
Workup
- temperatureThe reaction mixture was heated
- temperatureat reflux overnight
- washwashed with water (20 mL)
- extractionThe aqueous layer was extracted with dichloromethane (20 mL)
- dry with materialIt was dried over Na2SO4
- concentrationconcentrated
- customIt was purified by prep-TLC (Hexanes:ethyl acetate=10:1)
Sources & evidence
- ORD record
- ord-15b0cb679c6e40b9b4ea55fad329654c
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08623889B2
Reaction notes
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