Sodium Hydroxide → 3-Bromo-5-(methoxycarbonyl)benzoic acid

HRID 1397258Notes

Reaction equation

HRID 1397258 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([Br:14])[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.[OH-].[Na+]>CC(C)=O.O>[Br:14][C:12]1[CH:13]=[C:4]([CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=1)[C:3]([OH:15])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl ester

Product 1

HCID 225936413-Bromo-5-(methoxycarbonyl)benzoic acidYield 89.5%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

Dimethyl-5-bromoisophthalate (3 g, 11.0 mmol) was dissolved in acetone-H2O (2:1 v/v, 60 mL) and NaOH (0.40 g, 11.0 mmol) was added. The reaction mixture was allowed to stir for 4 h. Acetone was removed under reduced pressure and the aqueous layer was washed with EtOAc, acidified to pH ˜2-3 using 1.5N HCl, and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield 3-bromo-5-(methoxycarbonyl)benzoic acid (2.55 g, yield 89%): 1H NMR (300 MHz, DMSO-d6) δ 13.75 (br s, 1H), 8.40 (d, J=1.0 Hz, 1H), 8.26 (d, J=1.4 Hz, 1H), 8.23 (d, J=1.0 Hz, 1H), 3.89 (s, 3H). MS (ESI) m/z: Calculated for C9H7BrO4: 257.95. found: 258.0 (M+H)+.

Workup

  1. customAcetone was removed under reduced pressure
  2. washthe aqueous layer was washed with EtOAc
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dfc271aa91f248a1a72d7ad11a7ac1f2
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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