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

HRID 1747218Notes

Reaction equation

HRID 1747218 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 (0.74 mL, 14.4 mmol) was added to a RT suspension of 3-methoxy-4-methylbenzoic acid (2.0 g, 12 mmol) in acetic acid (15 mL) and water (15 mL) and the resulting mixture was heated to 60° C. for 2 h. The reaction mixture was cooled to RT and filtered rinsing with cold water (40 mL) to yield 2-bromo-5-methoxy-4-methylbenzoic acid as a white solid that was used further without purification. LC-MS A: tR=0.76 min, [M+H]+=No ionisation. 1H NMR (DMSO) δH: 7.49 (s, 1H), 7.29 (s, 1H), 3.82 (s, 3H), 2.17 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered
  3. washrinsing with cold water (40 mL)

Sources & evidence

ORD record
ord-215921d3433444e2bc602bca59a3e429
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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