Hydrochloric Acid → 4-Bromofuran-2-carboxylic acid

HRID 238718Notes

Reaction equation

HRID 238718 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([OH:10])=[O:9])[O:5][C:6]=1Br.[OH-].[NH4+].Cl>[Zn].O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([OH:10])=[O:9])[O:5][CH:6]=1

Participants

6

Procedure

A mixture of 4,5-dibromo-furan-2-carboxylic acid 22a (5.5 g, 20.3 mmol) and 18 mL of ammonium hydroxide was added to 63 mL of water followed by addition of zinc powder (1.46 g, 22.33 mmol). Upon completion of the addition, the reaction mixture was stirred at room temperature for 6 hours. The mixture was adjusted to pH 3 with 1 M hydrochloric acid to form a great quantity of precipitates. The mixture was filtered and the filter cake was washed with n-hexane (15 mL×4) and dried to obtain the title compound 4-bromo-furan-2-carboxylic acid 22b (3.2 g, yield 83.1%) as a white solid.

Workup

  1. additionUpon completion of the addition
  2. customto form a great quantity
  3. customof precipitates
  4. filtrationThe mixture was filtered
  5. washthe filter cake was washed with n-hexane (15 mL×4)
  6. customdried

Sources & evidence

ORD record
ord-da297a649124435799ac7206f0ba7e33
Source dataset
uspto-grants-2014_02
Patent number
US08642637B2

Reaction notes

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