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

HRID 1257523Notes

Reaction equation

HRID 1257523 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].[OH-].[Na+]>CO.O1CCCC1>[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 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 5-bromoisophthalate (6.2 g, 22.7 mmol) in methanol (10 mL) and tetrahydrofuran (10 mL) was added dropwise NaOH (1.0 M in water; 20.4 mL, 20.4 mmol). The reaction mixture was stirred at ambient temperature. After 18 h, the mixture was concentrated. Ethyl acetate was added and the mixture was extracted with water (2×). The combined aqueous layer was adjust to pH=3 using HCl (6.0 M in water). This mixture was extracted with ethyl acetate (2×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated (4.9 g).

Workup

  1. concentrationthe mixture was concentrated
  2. additionEthyl acetate was added
  3. extractionthe mixture was extracted with water (2×)
  4. extractionThis mixture was extracted with ethyl acetate (2×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated (4.9 g)

Sources & evidence

ORD record
ord-92429c59aa084233af39710bdec08d36
Source dataset
uspto-grants-2013_06
Patent number
US08461185B2

Reaction notes

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