Bromine → 5-(2-Bromo-acetyl)-4'-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

HRID 506631Notes

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]>C(Cl)(Cl)(Cl)Cl>[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

Conditions

Temperature: 45 °C

Procedure

A solution of bromine (0.074 ml, 1.5 mmol) dissolved in CCl4 (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 CCl4 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-b8393eff06274d0c883014b6055126a7
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786110B2

Reaction notes

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