Bromine → 2-Bromo-4-chloro-5-methoxybenzoic acid

HRID 1428929Notes

Reaction equation

HRID 1428929 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].[Br:13]Br>CC(O)=O.O>[Br:13][C:9]1[CH:10]=[C:2]([Cl:1])[C:3]([O:11][CH3:12])=[CH:4][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 24408BromineHCID 20633784-Chloro-3-methoxybenzoic acid

Product 1

HCID 848076632-Bromo-4-chloro-5-methoxybenzoic acidYield 70.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 4-chloro-3-methoxybenzoic acid (5.0 g, 26.7 mmol) in HOAc (25 mL) and water (25 mL) was treated slowly with Br2 (1.6 mL 32 mmol). After heating to 60° C. for 2 h, the reaction was stirred cooled to rt overnight. It was quenched with water (300 mL), and the precipitate was filtered and dried to yield 2-bromo-4-chloro-5-methoxybenzoic acid (5.0 g, 70%). (264.87 [M−H]) 1H NMR: (400 MHz, DMSO) δ: 3.90 (s, 3H), 7.46 (s, 1H), 7.82 (s, 1H), 13.63 (s, 1H).

Workup

  1. temperaturecooled to rt overnight
  2. customIt was quenched with water (300 mL)
  3. filtrationthe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-29b23325237e4dcba2536df9c7e99f96
Source dataset
uspto-grants-2015_01
Patent number
US08937178B2

Reaction notes

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