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

HRID 1436631

Reaction equation

HRID 1436631 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5](=[O:17])[C:6]1[CH:15]=[C:14]([Br:16])[CH:13]=[C:8]([C:9]([O:11]C)=[O:10])[CH:7]=1.BrC1C=C(C(O)=O)C=C(C=1)C(O)=O>CO>[CH3:3][O:4][C:5](=[O:17])[C:6]1[CH:15]=[C:14]([Br:16])[CH:13]=[C:8]([C:9]([OH:11])=[O:10])[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 900735-Bromoisophthalic acidHCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add a solution of NaOH pellets (3.66 g, 91.5 mmol) in methanol (200 mL) to dimethyl-5-bromoisophthalate (25 g) and stir the resulting solution overnight at room temperature. Add water (300 mL) and extract with dichloromethane (3×200 mL). Acidify the aqueous with 5 N HCl (20 mL), filter the precipitate and dry to give a mixture of the title compound and 5-bromo-isophthalic acid in about a 6:4 ratio by LCMS (18.2 g crude).

Workup

  1. extractionAdd water (300 mL) and extract with dichloromethane (3×200 mL)
  2. filtrationfilter the precipitate
  3. customdry
  4. customto give

Sources & evidence

ORD record
ord-40960b307c61456d9b46c0fd87310bf3
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Linked notes

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