Sodium Hydroxide → 5-Bromo-2-methylfuran-3-carboxylic acid

HRID 2099545Notes

Reaction equation

HRID 2099545 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:11]=[C:10]([Br:12])[O:9][C:8]=1[CH3:13])=[O:6]>O.CO>[Br:12][C:10]1[O:9][C:8]([CH3:13])=[C:7]([C:5]([OH:6])=[O:4])[CH:11]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15534190Methyl 5-bromo-2-methylfuran-3-carboxylate

Product 1

HCID 230399205-Bromo-2-methylfuran-3-carboxylic acidYield 8.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (4.5 g) in water (10 ml) was added to a stirred solution of 5-bromo-2-methyl-furan-3-carboxylic acid methyl ester (5 g, 233 mmoles) in methanol (70 ml) and the mixture was stirred at room temperature for 16 hours. The solvent was evaporated and the residue was diluted with water (10 ml) and acidified to pH2 with 1M aqueous hydrochloric acid. The precipitate was collected, washed with water, dried at 40° C. to afford 5-Bromo-2-methyl-furan-3-carboxylic acid (14)(4 g). LC/MS System A; Rt=2.86 min.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with water (10 ml)
  3. customThe precipitate was collected
  4. washwashed with water
  5. customdried at 40° C.

Sources & evidence

ORD record
ord-4c4c92006b7d40b7a20c6966a8d124db
Source dataset
uspto-grants-2009_08
Patent number
US07569602B2

Reaction notes

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