3,5-Dimethylchlorobenzene → 1-(Bromomethyl)-3-chloro-5-methylbenzene

HRID 426122

Reaction equation

HRID 426122 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH:3]=1.[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.[W]>[Br:10][CH2:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 2

HCID 328873,5-DimethylchlorobenzeneHCID 67184N-bromobutanimide

Product 1

HCID 123755491-(Bromomethyl)-3-chloro-5-methylbenzeneYield 68%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

The mixture of 1-Chloro-3,5-dimethyl-benzene (32 g, 0.23 mol) and N-bromosuccinimide (40.5 g, 0.23M) in carbon tetrachloride (400 ml) was refluxed for 3 hr under a light of 500 W tungsten light. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, hexane) to afford 33 g (68%) of a white solid. 1H NMR (200 MHz, CDCl3) δ: 2.32 (3H, s), 4.39 (2H, s), 7.10 (2H, s), 7.18 (1H, s).

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customthe residue was purified by silica gel column chromatography (eluent, hexane)

Sources & evidence

ORD record
ord-4fa415f113bc427290a74a36b5a339d3
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Linked notes

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