Carbon tetrabromide → 4-Nitrobenzyl bromide

HRID 987038Notes

Reaction equation

HRID 987038 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-20109dca475b44769005f05763ca0c17
Source dataset
uspto-grants-2003_10
Patent number
US06630461B2

Reaction notes

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