Benzoyl Peroxide → 2-Bromomethyl-4'-chloro-biphenyl-4-carboxylic acid methyl ester

HRID 270962Notes

Reaction equation

HRID 270962 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[C:7]([CH3:18])[CH:6]=1)=[O:4].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:37]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[C:7]([CH2:18][Br:37])[CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 58610225Methyl 4'-chloro-2-methyl[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 691546302-Bromomethyl-4'-chloro-biphenyl-4-carboxylic acid methyl esterYield 55.8%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 191 mg (0.73 mmol) of 4′-chloro-2-methyl-biphenyl-4-carboxylic acid methyl ester in 4 mL of carbon tetrachloride (CCl4) was added 9.7 mg (0.04 mmol) of benzoyl peroxide, followed by 124 mg (0.696 mmol) of N-bromosuccinimide (NBS), and the reaction mixture was heated at reflux for 6 h. The mixture was cooled to rt, diluted with dichloromethane and washed with water and brine. The organic layer was dried over sodium sulfate and concentrated to give 132 mg (53%) of 2-bromomethyl-4′-chloro-biphenyl-4-carboxylic acid methyl ester, as an oil, which was used without any further purification in the next step. 1H NMR δCDCl3 8.10 (s, 1H), 7.91-7.89 (d, J=8.0 Hz, 1-H), 7.37-7.35 (d, J=8.3 Hz, 2H), 7.30-7.18 (d, J=8.7 Hz, 2H), 7.22-7.20 (d, J=8.0 Hz, 1H), 4.30 (s, 2H), 3.87 (s, 3H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 6 h
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9ebb2893ae0d490ba725e6f4bb546f58
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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