Bromine → 5-(2-Bromo-acetyl)-4'-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide
Reaction equation
[Br:1]Br.[CH3:3][O:4][CH2:5][CH:6]([NH:8][C:9]([C:11]1[CH:12]=[C:13]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[CH:14]=[C:15]([C:17](=[O:19])[CH3:18])[CH:16]=1)=[O:10])[CH3:7]>>[CH3:3][O:4][CH2:5][CH:6]([NH:8][C:9]([C:11]1[CH:12]=[C:13]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[CH:14]=[C:15]([C:17](=[O:19])[CH2:18][Br:1])[CH:16]=1)=[O:10])[CH3:7]Participants
3
Conditions
- Temperature
- 45 °C
Procedure
A solution of bromine (0.074 ml, 1.5 mmol) dissolved in CCI4 (2.0 ml) was added slowly to a stirred solution of 5-acetyl-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide (325 mg, 1 mmol) in 3.0 ml of CCI4 at room temperature. The mixture was then heated to 45° C. for 14 hours. The solution was cooled and extracted with EtOAc, and the combined organic layers were washed with saturated aqueous Na2S2O3, brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting crude 5-(2-bromo-acetyl)-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide was used for next step directly without further purification.
Workup
- temperatureThe solution was cooled
- extractionextracted with EtOAc
- washthe combined organic layers were washed with saturated aqueous Na2S2O3, brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resulting crude 5-(2-bromo-acetyl)-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide was used for next step directly without further purification
Sources & evidence
- ORD record
- ord-267563e490594e60aa57cec3042ef99c
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501933B2
Reaction notes
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