Carbon tetrabromide → 1-(3-Bromopropyl)-1H-imidazole

HRID 1767736Notes

Reaction equation

HRID 1767736 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8]O)[CH:5]=[CH:4][N:3]=[CH:2]1.C(Br)(Br)(Br)[Br:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[Br:11][CH2:8][CH2:7][CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 47122713-(1H-imidazol-1-yl)propan-1-ol

Product 1

HCID 120386541-(3-Bromopropyl)-1H-imidazoleYield 61.6%

Procedure

A mixture of 1H-imidazole-1-propanol (1.00 g, 3.65 mmol—prepared according to patent: WO 9722596 A1), carbon tetrabromide (1.80 g, 5.47 mmol) and triphenyl phosphine (1.43 g, 5.47 mmol) was stirred at ambient temperature for 18 hours. The solvent was evaporated and the residue purified by flash chromatography on silica gel. Elution with 10% methanol in dichloromethane yielded the title compound (425 mg, 35% yield) as a pale yellow solid:

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by flash chromatography on silica gel
  3. washElution with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-c88d35f8004943bfaf269eff9d40a285
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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