Carbon tetrabromide → 4-Bromo-1-(bromomethyl)-2-methylbenzene

HRID 216709Notes

Reaction equation

HRID 216709 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[C:4]([CH3:10])[CH:3]=1.C(Br)(Br)(Br)[Br:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:12])=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22280088(4-Bromo-2-methylphenyl)methanol

Product 1

HCID 225690184-Bromo-1-(bromomethyl)-2-methylbenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-Bromo-2-methyl-phenyl)-methanol (as obtained in preparation 25) (4.58 g, 22.8 mmol) in CH2Cl2 (50 ml) is added, under Argon and at RT, carbon tetrabromide (9.27 g, 27.4 mmol) followed by triphenylphosphine (7.25 g, 27.4 mmol). The mixture is stirred overnight and then concentrated in vacuo. The crude residue is then purified by chromatography (silicagel, hexane:EtOAc 25:1) to afford the title compound as a clear oil.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude residue is then purified by chromatography (silicagel, hexane:EtOAc 25:1)

Sources & evidence

ORD record
ord-8425ad05259042d4b6c8c395a867b1f5
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Reaction notes

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