N-bromobutanimide → Ethyl 2-(bromomethyl)biphenyl-4-carboxylate

HRID 731927Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1C(=O)N([Br:26])C(=O)C1>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:26][CH2:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 90 °C

Procedure

In 130 ml of carbon tetrachloride was dissolved 10 g of ethyl 2-methylbiphenyl-4-carboxylate, the whole was heated to 90° C. and then 1.0 g of NBS and 136 mg of 2,2′-azobisisobutyronitrile were added thereto. After the reaction solution was heated under reflux, 6.78 g of NBS was added thereto and the whole was heated under reflux for 1 hour and a half. After the reaction solution was cooled to room temperature, precipitate was removed by filtration, water was added to the filtrate, and the organic layer was extracted with carbon tetrachloride. After the resulting organic layer was dried over anhydrous magnesium sulfate, the solvent was removed by evaporation to obtain 13.6 g of ethyl 2-(bromomethyl)biphenyl-4-carboxylate as a white solid.

Workup

temperatureAfter the reaction solution was heated
temperatureunder reflux
temperaturethe whole was heated
temperatureunder reflux for 1 hour
temperatureAfter the reaction solution was cooled to room temperature
customprecipitate was removed by filtration, water
additionwas added to the filtrate
extractionthe organic layer was extracted with carbon tetrachloride
dry with materialAfter the resulting organic layer was dried over anhydrous magnesium sulfate
customthe solvent was removed by evaporation

Sources & evidence

ORD record: ord-145528f9e8a64739a3104fd160de4055
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585878B2

Reaction notes

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