Hydrochloric Acid → 4-Bromofuran-2-carboxylic acid

HRID 2271452Notes

Reaction equation

HRID 2271452 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-b35302e8832b40cc80fb46ee36935382
Source dataset
uspto-grants-2015_09
Patent number
US09120762B2

Reaction notes

Loading…