N-bromobutanimide → 5-(Bromomethyl)-α-methyl-2-nitrobenzenemethanol

HRID 1732078Notes

Reaction equation

HRID 1732078 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[Br:14]N1C(=O)CCC1=O>>[Br:14][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:8]([OH:10])[CH3:9])[CH:7]=1

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 11769120HCID 11769120, compound

Product 1

HCID 202265155-(Bromomethyl)-α-methyl-2-nitrobenzenemethanol

Procedure

Compound 2 is synthesized in two steps from 1-(5-methyl-2-nitrophenyl) ethanone (1), which can be obtained as described by Doppler et al. (1979) Helv. Chem. Acta 62:291-303. Specifically, the ring methyl group is brominated using N-bromosuccinimide and then the benzylic ketone is reduced to an alcohol. Those procedures are described below.

Workup

  1. customcan be obtained

Sources & evidence

ORD record
ord-4b37a79c79a94d5bb2f61fd5cc7a7955
Source dataset
uspto-grants-1986_11
Patent number
US04625014

Reaction notes

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