Carbon tetrabromide → 4-(Bromomethyl)-1-chloro-2-iodobenzene

HRID 1610930Notes

Reaction equation

HRID 1610930 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]O)=[CH:23][C:22]=1[I:29].C(Br)(Br)(Br)[Br:31]>ClCCl>[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][Br:31])=[CH:23][C:22]=1[I:29]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 13636476(4-Chloro-3-iodophenyl)methanol

Product 1

HCID 156895474-(Bromomethyl)-1-chloro-2-iodobenzeneYield 139.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (1.1 g) was added in portions to a solution of 4-chloro-3-iodobenzyl alcohol (1.1 g) in dichloromethane (40 ml) at 0° C. and stirring was continued for 10 minutes. Carbon tetrabromide (1.5 g) was then added in portions over 2 minutes, the reaction mixture was allowed to warm to ambient temperature and was stirred for 15 hours. The solution was added directly to a silica charged chromatography column and was eluted with dichloromethane to give 4-chloro-3-iodobenzyl bromide (1.9 g). NMR (CD3SOCD3): d 4.6 (s, 2H), 7.5 (m, 2H), 7.6 (s, 1H), 8.0 (m, 1H).

Workup

  1. stirringwas stirred for 15 hours
  2. additionThe solution was added directly to a silica
  3. additioncharged chromatography column
  4. washwas eluted with dichloromethane

Sources & evidence

ORD record
ord-7e0b4e434db2494aa3536ae8b8b3cc58
Source dataset
uspto-grants-2006_01
Patent number
US06984657B1

Reaction notes

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