Methyl Salicylate → Methyl 5-bromosalicylate

HRID 1596439Notes

Reaction equation

HRID 1596439 reaction equation
[Br:1]Br.[C:3]([O:12][CH3:13])(=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:6]>C(O)(=O)C>[Br:1][C:9]1[CH:8]=[CH:7][C:5]([OH:6])=[C:4]([CH:10]=1)[C:3]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 4133Methyl SalicylateHCID 24408Bromine

Product 1

HCID 77683Methyl 5-bromosalicylateYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Br2 (52 g) was slowly added to a stirred solution of methyl salicylate (50 g; 330 mmol) in 300 mL acetic acid. The reaction mixture was stirred at rt. for 10 h, poured on ice-water and the precipitate recrystallized from MeOH, giving the sub-title compound in a 83% yield.

Workup

  1. additionpoured on ice-water
  2. customthe precipitate recrystallized from MeOH

Sources & evidence

ORD record
ord-4723fe0e3a0c486c88a0b3ec071a587b
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

Loading…