N-bromobutanimide → N-t-Butyl-4'-bromomethylbiphenyl-2-carboxamide
Reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([NH:13][C:14]([C:16]1[C:17]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[C:9]([NH:13][C:14]([C:16]1[C:17]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][Br:1])=[CH:24][CH:23]=2)=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10]Participants
5
Procedure
4.39 g of N-bromosuccinimide and 50 mg of benzoyl peroxide were added to a solution of 6.00 g of N-t-butyl-4'-methylbiphenyl-2-carboxamide [prepared as described in Preparation 38(i)] in 90 ml of carbon tetrachloride, and the mixture was heated under reflux for 4 hours. At the end of this time, the reaction mixture was cooled to room temperature, washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1:4 by volume mixture of ethyl acetate and hexane as the eluent, to give 7.04 g of the title compound as crystals, melting at 124°-126° C.
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 4 hours
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated by evaporation under reduced pressure
- customThe residue was purified by column chromatography through silica gel
- additionby volume mixture of ethyl acetate and hexane as the eluent
Sources & evidence
- ORD record
- ord-73149aa28a4744aaaf29219f9aa37e9b
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05646171
Reaction notes
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