Chloroform → 1-(Bromomethyl)-4-chloro-2-nitrobenzene

HRID 597135

Reaction equation

HRID 597135 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:5]=1[CH2:6]O)([O-:3])=[O:2].C(Cl)(Cl)Cl.P(Br)(Br)[Br:18]>O>[N+:1]([C:4]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:5]=1[CH2:6][Br:18])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24614Phosphorus tribromideHCID 899564-Chloro-2-nitrobenzyl alcohol

Product 1

HCID 105868161-(Bromomethyl)-4-chloro-2-nitrobenzeneYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 16.5 g. of 2-nitro-4-chlorobenzyl alcohol in 200 ml. of chloroform was added dropwise 13 g. of phosphorus tribromide, and the mixture was heated to reflux for 1 hour on a water bath. The reaction mixture was then poured into water, and the chloroform layer was separated and washed with water. After the solvent was removed, the residue was extracted with ligroin while warming and allowed to stand to form colorless acicular crystals of 2-nitro-4-chlorobenzyl bromide (80% yield) melting at 42° to 43° C.

Workup

  1. temperatureto reflux for 1 hour on a water bath
  2. customthe chloroform layer was separated
  3. washwashed with water
  4. customAfter the solvent was removed
  5. extractionthe residue was extracted with ligroin
  6. temperaturewhile warming

Sources & evidence

ORD record
ord-a0537214ec96402ca5b697f29eb4e3a1
Source dataset
uspto-grants-1977_03
Patent number
US04013639

Linked notes

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