Bromine → 2-Bromo-5-methoxy-4-methylbenzoic acid

HRID 1477742Notes

Reaction equation

HRID 1477742 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:8]([OH:10])=[O:9]>C(O)(=O)C.O>[Br:1][C:11]1[CH:12]=[C:13]([CH3:14])[C:5]([O:4][CH3:3])=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 24408BromineHCID 815794-Methyl-m-anisic acid

Product 1

HCID 2916782-Bromo-5-methoxy-4-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Br2 (1.11 mL, 21.7 mmol) was added to a rt suspension of 3-methoxy-4-methylbenzoic acid (3.00 g, 18.1 mmol) in a mixture of acetic acid (23 mL) and water (23 mL) and the mixture was heated to 60° C. for 2 h. The mixture was allowed to reach rt and the solids were filtered and rinsed with water to yield 2-bromo-5-methoxy-4-methylbenzoic acid as a white solid which was used as such in the next step. LC-MS A: tR=0.76 min, no ionization.

Workup

  1. customto reach rt
  2. filtrationthe solids were filtered
  3. washrinsed with water

Sources & evidence

ORD record
ord-daddc81dde5b4d04b0f6b066c502c42d
Source dataset
uspto-grants-2016_08
Patent number
US09403813B2

Reaction notes

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