Water → 3-Bromo-5-(methoxycarbonyl)benzoic acid

HRID 1771711Notes

Reaction equation

HRID 1771711 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]([O:14]C)=[O:13])[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=1.O[Li].O.O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=1)[C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl esterHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 225936413-Bromo-5-(methoxycarbonyl)benzoic acidYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl 5-bromobenzene-1,3-dicarboxylate (5 g, 18.3 mmol, 1.0 eq) was dissolved in THF (50 mL) and LiOH.H2O (1.1 g, 27.5 mmol, 1.5 eq) and H2O (10 mL) were added. The mixture was stirred at room temperature overnight. The THF was removed in vacuo and the aqueous phase acidified with diluted HCl. The aqueous phase was extracted with EtOAc, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (CH2Cl2:MeOH, 50:1) to give the title compound as a white solid (3 g, 63%).

Workup

  1. customThe THF was removed in vacuo
  2. extractionThe aqueous phase was extracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue obtained
  7. customwas purified by column chromatography (CH2Cl2:MeOH, 50:1)

Sources & evidence

ORD record
ord-80414146020d4abbbf93b536e90ca54e
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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