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

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

Reactant 2

HCID 11205Carbon tetrabromide

HCID 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

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

Sources & evidence

ORD record: ord-df78e76843d643378c0d27fe69b0f4e7
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629168B2

Reaction notes

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