Carbon tetrabromide → 3-Methoxy-4-nitrobenzyl bromide

HRID 1934721Notes

Reaction equation

HRID 1934721 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH2:6]O.C(Br)(Br)(Br)[Br:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH2:6][Br:15]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 6029613-Methoxy-4-nitrobenzyl alcohol

Product 1

HCID 126216043-Methoxy-4-nitrobenzyl bromideYield 120.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mitre of 3-methoxy-4-nitrobenzyl alcohol (3.00 g) and carbon tetrabromide (8.15 g) in dichloromethane (60 mL) was added triphenylphosphine (5.16 g) under ice-water cooling, and the mixture was stirred for an hour at ambient temperature. After evaporation of the solvent, the residue was purified by a silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (5:1) to give 3-methoxy-4-nitrobenzyl bromide as pale yellow powders (4.87 g).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was purified by a silica gel column chromatography
  3. washeluting with a mixture of hexane and ethyl acetate (5:1)

Sources & evidence

ORD record
ord-509af0281a444b998d0e1408a422f1b5
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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