Triphenylphosphine → HCID 68157796, compound

HRID 242780Notes

Reaction equation

HRID 242780 reaction equation
[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:16]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C(=O)N([Br:44])C(=O)C1>C(Cl)Cl>[Br:44][CH2:16][C:8]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 13024895HCID 13024895, compound

Product 1

HCID 68157796HCID 68157796, compoundYield 217.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (1-phenyl-1H-benzoimidazol-2-yl)methanol (240 mg, 1.02 mmol) and triphenylphospine (295 mg, 1.12 mmol) in DCM (10 mL) was added NBS (200 mg, 1.12 mmol) and the mixture was stirred at RT for 3 h. Volatiles were evaporated under reduced pressure and the residue was purified by column chromatography (Si—PCC, gradient 0-5% MeOH in DCM) affording 2-Bromomethyl-1-phenyl-1H-benzoimidazole as a colourless oil (0.636 g, quantitative yield). LCMS: RT 3.31 min [M+H]+ 386.8/388.8

Workup

  1. customVolatiles were evaporated under reduced pressure
  2. customthe residue was purified by column chromatography (Si—PCC, gradient 0-5% MeOH in DCM)

Sources & evidence

ORD record
ord-471e1b4b4bde4020a70d84a0a833aeda
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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