Hydrochloric Acid → 3-Bromo-5-(methoxycarbonyl)benzoic acid

HRID 1845177Notes

Reaction equation

HRID 1845177 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]([O:14]C)=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=1)[C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl esterHCID 17749109Barium hydroxide, octahydrate

Product 1

HCID 225936413-Bromo-5-(methoxycarbonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a round-bottom flask were charged with dimethyl 5-bromoisophthalate (0.50 g, 1.8 mmol), barium hydroxide octahydrate (0.43 g, 1.4 mmol) and methanol (10 mL). The mixture was stirred at room temperature overnight. HCl (2 N ethyl ether solution, 10 mL) was added and the volatiles were removed under reduced pressure. The residue was purified via flash chromatography to afford the desired product as a white solid. 1H NMR (400 MHz, DMSO-d6): 13.70 (br, 1H), 8.42 (t, J=1.5 Hz, 1H), 8.31-8.24 (m, 2H), 3.90 (s, 3H).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customThe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-939e4a2a2f73460391382ab7f5f89ef8
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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