Triphenylphosphine → 4-Bromomethyl-2-methoxy-biphenyl

HRID 1166293Notes

Reaction equation

HRID 1166293 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:16]=[C:15]([CH2:17]O)[CH:14]=[CH:13][C:12]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:1][CH2:17][C:15]1[CH:14]=[CH:13][C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([O:10][CH3:9])[CH:16]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 22997534(2-Methoxy-biphenyl-4-yl)-methanol

Product 1

HCID 229975474-Bromomethyl-2-methoxy-biphenyl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.24 g (7.6 mmol) of NBS (N-bromosuccinimide) is added in small portions to a solution of (2-methoxy-biphenyl-4-yl)-methanol (1.35 g, 6.3 mmol) and triphenyl phosphine (2.0 g, 7.0 mmol) in 15 mL of CH2Cl2 at 0° C. The cooling bath is removed and the reaction mixture is stirred at room temperature overnight. The reaction mixture is then concentrated in vacuo, and the residue is purified by chromatography on silica gel (10% EtOAc/hexane) to furnish 4-bromomethyl-2-methoxy-biphenyl as a clear, colorless oil. 1H NMR (250 MHz, CDCl3) δ 7.45-7.55 (m, 2H), 7.20-7.45 (m, 4H), 7.05 (dd, 2H), 7.0 (d, 1H), 4.50 (s, 2H), 3.80 (s, 3H).

Workup

  1. customThe cooling bath is removed
  2. concentrationThe reaction mixture is then concentrated in vacuo
  3. customthe residue is purified by chromatography on silica gel (10% EtOAc/hexane)

Sources & evidence

ORD record
ord-4d917f6c7e9c4db9afc328dd074338b4
Source dataset
uspto-grants-2003_09
Patent number
US06613782B2

Reaction notes

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