Hydrogen Bromide → 2-(Bromomethyl)-4-methyl-1-nitrobenzene

HRID 1264597Notes

Reaction equation

HRID 1264597 reaction equation
[BrH:1].[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH:10]=1)[CH2:8]O>C(O)(=O)C>[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH:10]=1)[CH2:8][Br:1]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 568847(5-Methyl-2-nitrophenyl)methanol

Product 1

HCID 137762802-(Bromomethyl)-4-methyl-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a cooled (ice-water bath) mixture of 30% HBr in acetic acid (3 ml) was added 2.5 g 5-methyl-2-nitrobenzyl alcohol and the chilled solution stirred for 2 hours. The mixture was poured into ice-water and extracted with diethyl ether. The extract was washed with H2O, brine and the solvent removed under vacuum to give a mixture of product (50%) and starting material (50%).

Workup

  1. temperatureTo a cooled
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with H2O, brine
  4. customthe solvent removed under vacuum
  5. customto give

Sources & evidence

ORD record
ord-5ee68db543654f1f8a74c0e4c242249e
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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