Thiophene-3-carboxylic acid → 5-Bromothiophene-3-carboxylic acid

HRID 628238Notes

Reaction equation

HRID 628238 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1.[Br:9]Br>C(O)(=O)C>[Br:9][C:5]1[S:1][CH:2]=[C:3]([C:6]([OH:8])=[O:7])[CH:4]=1

Participants

4

Reactant 2

HCID 6918Thiophene-3-carboxylic acidHCID 24408Bromine

Product 1

HCID 120399785-Bromothiophene-3-carboxylic acidYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Under a nitrogen atmosphere, 3-thiophenecarboxylic acid (10 g, 78 mmol) was added to acetic acid (100 ml), and bromine (12.5 g, 78 mmol) was then slowly dropped and stirred at the same temperature for one hour. Then, ice (300 g) was added. By filtering a precipitated white solid and then drying the white solid after washing with water, a target substance was obtained as a white solid (80% yield). 1H-NMR (400 MHZ, CDCl3, TMS) δ 8.12 (s, 1 H), 7.51 (s, 1 H)

Workup

  1. additionwas then slowly dropped
  2. filtrationBy filtering a precipitated white solid
  3. customdrying the white solid
  4. washafter washing with water

Sources & evidence

ORD record
ord-c2580f4780f44bd095275368034c4f89
Source dataset
uspto-grants-2016_04
Patent number
US09312491B2

Reaction notes

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