Carbon tetrabromide → 4-Nitrobenzyl bromide

HRID 1356425Notes

Reaction equation

HRID 1356425 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Br)(Br)(Br)[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:13][CH2:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 692754-Nitrobenzyl alcohol

Product 1

HCID 660114-Nitrobenzyl bromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-nitrobenzyl alcohol (6 g, 39 mmoles) is put into solution in dichloromethane (100 ml) and carbon tetrabromide (14.9 g, 45 mmoles) is added. Triphenylphosphine (11.8 g, 45 mmoles) is added in portions to the medium at 0° C. Then the mixture is agitated for 2 hours at ambient temperature. The solvent is evaporated off and the product obtained is purified on silica gel in an ethyl acetate/heptane mixture (1/2). It is obtained in the form of white needle-shaped crystals (7.2 g; 85%). Melting point: 97-98° C.

Workup

  1. customThe solvent is evaporated off
  2. customthe product obtained
  3. customis purified on silica gel in an ethyl acetate/heptane mixture (1/2)
  4. customIt is obtained in the form of white needle-shaped crystals (7.2 g; 85%)

Sources & evidence

ORD record
ord-970f029ec5ed4f4382b748667025a761
Source dataset
uspto-grants-2003_07
Patent number
US06586454B2

Reaction notes

Loading…