Carbon tetrabromide → 1-(Bromomethyl)-2-methyl-4-nitrobenzene

HRID 469837Notes

Reaction equation

HRID 469837 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11]O.C(Br)(Br)(Br)[Br:14]>>[Br:14][CH2:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[CH3:1]

Participants

3

Reactant 2

HCID 11205Carbon tetrabromideHCID 21345674(2-Methyl-4-nitrophenyl)methanol

Product 1

HCID 126541471-(Bromomethyl)-2-methyl-4-nitrobenzene

Procedure

To a solution of 4.55 g (27.2 mmol) (2-methyl-4-nitro-phenyl)-methanol 10.8 g (40.8 mmol) triphenylphosphine and 13.7 g (40.8 mmol) carbon tetrabromide is added at 0° C. The reaction mixture is stirred at room temperature for 1 h. After that the reaction mixture is filtered and the filtrate is concentrated in vacue. The residue is purified by chromatography (silicagel, 100% hexane=>100% EtOAc) to afford the title compound as an oil.

Workup

  1. filtrationAfter that the reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacue
  3. customThe residue is purified by chromatography (silicagel, 100% hexane=>100% EtOAc)

Sources & evidence

ORD record
ord-df78e76843d643378c0d27fe69b0f4e7
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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