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

HRID 1018974Notes

Reaction equation

HRID 1018974 reaction equation
[CH3:1][O:2][P:3]([C:7]1[CH:8]=[C:9]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21]C(N3C4C=CC=CC=4N=N3)(C3C=CC=CC=3)CC3C=CC(CP(OF)(OF)=O)=CC=3)=[CH:17][CH:16]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])(=[O:6])[O:4][CH3:5].[Br:52][Si](C)(C)C>C(Cl)Cl>[CH3:1][O:2][P:3]([C:7]1[CH:8]=[C:9]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][Br:52])=[CH:17][CH:16]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])(=[O:6])[O:4][CH3:5]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 881620004'-{2-Benzotriazol-1-yl-3-[4-(difluorophosphonomethy)phenyl]-2-phenylpropyl}-4-methoxybiphenyl-3-yl-phosphonic acid dimethyl ester

Product 1

HCID 599208374'-bromomethyl-4-methoxybiphenyl-3-yl-phosphonic Acid Dimethyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4′-{2-benzotriazol-1-yl-3-[4-(difluorophosphonomethy)phenyl]-2-phenylpropyl}-4-methoxybiphenyl-3-yl-phosphonic acid dimethyl ester (330 mg, 0.39 mmol) and bromotrimethylsilane (1 mL) in CH2Cl2 (5 mL) was stirred at r.t. overnight. Volatile mateials were removed in vacuo. The residue was co-evaporated with ˜90% aqueous EtOH (3×) to give the title compound as a light brown foam.

Workup

  1. customVolatile mateials were removed in vacuo

Sources & evidence

ORD record
ord-b1decc4e61984948b6b19a2ef2674891
Source dataset
uspto-grants-2002_11
Patent number
US06486141B2

Reaction notes

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