Benzoyl Peroxide → 4'-bromomethyl-4-methoxybiphenyl-3-yl-phosphonic Acid Dimethyl Ester

HRID 1018973Notes

Reaction equation

HRID 1018973 reaction equation
[CH3:1][O:2][P:3]([C:7]1[CH:8]=[C:9]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])(=[O:6])[O:4][CH3:5].[Br:22]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[CH3:1][O:2][P:3]([C:7]1[CH:8]=[C:9]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][Br:22])=[CH:19][CH:20]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])(=[O:6])[O:4][CH3:5]

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 599208424-methoxy-4'-methylbiphenyl-3-yl-phosphonic Acid Dimethyl Ester

Product 1

HCID 599208374'-bromomethyl-4-methoxybiphenyl-3-yl-phosphonic Acid Dimethyl EsterYield 67%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-methoxy-4′-methylbiphenyl-3-yl-phosphonic acid dimethyl ester (300 mg, 1.1 mmol), N-bromosuccinimide (190 mg, 1.1 mmol) and a few crystal of benzoyl peroxide in CCl4 (15 mL) was refluxed and irradiated with a sun lamp for 1 h. More N-bromosuccinimde (30 mg, 0.17 mmol) was added and the mixture was refluxed for 30 min. After cooling to r.t., the mixture was diluted with CH2Cl2 and washed with H2O (3×), dried (MgSO4) and concentrated. The solid residue was swished with Et2O to give 280 mg (67%) of the title compound as a white solid.

Workup

  1. customirradiated with a sun lamp for 1 h
  2. additionMore N-bromosuccinimde (30 mg, 0.17 mmol) was added
  3. temperaturethe mixture was refluxed for 30 min
  4. washwashed with H2O (3×)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b30224cd05d84b1688c79aa0a9b06760
Source dataset
uspto-grants-2002_11
Patent number
US06486141B2

Reaction notes

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