Carbon tetrabromide → HCID 53704481, compound

HRID 1533274Notes

Reaction equation

HRID 1533274 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([CH2:13]O)[N:10]=[C:9]1[CH2:15][CH2:16][CH2:17][CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:39]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([CH2:13][Br:39])[N:10]=[C:9]1[CH2:15][CH2:16][CH2:17][CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 54365125HCID 54365125, compound

Product 1

HCID 53704481HCID 53704481, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-tert-butoxycarbonyl-2-n-butyl-4-(hydroxymethyl)imidazole (4.43 g) in dichloromethane (80 ml) was added triphenylphosphine (5.48 g) followed by carbon tetrabromide (6.93 g) at ambient temperature and the mixture was stirred for 30 minutes. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=4:1) to give 1-tert-butoxycarbonyl-2-n-butyl-4-(bromomethyl)imidazole (5.09 g) as a colorless oil.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-399e8f03a9844586a54735b5ba6b1179
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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