Hydrogen Bromide → 5-Bromothiophene-3-carboxylic acid

HRID 1879827Notes

Reaction equation

HRID 1879827 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1.Br.C1C=C[NH+]=CC=1.[Br:16][Br-]Br>CC(O)=O>[Br:16][C:5]1[S:1][CH:2]=[C:3]([C:6]([OH:8])=[O:7])[CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 6918Thiophene-3-carboxylic acid

Product 1

HCID 120399785-Bromothiophene-3-carboxylic acidYield 61.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of thiophene-3-carboxylic acid (12.6 g, 0.1 mol) in AcOH (96 ml), being stirred at room temperature, HBr solution (8 ml) was added, and the stirring continued until the color of mixture turned to yellow. Pyridinium bromide perbromide (27 g) was then sequentially added. The mixture was poured into ice-water, stirred for about 30 minutes. A white precipitate was formed, which was filtered and dried to obtain 5-bromo-thiophene-3-carboxylic acid (10.8 g) as a white solid after crystallization in hot water. HPLC: 92%.

Workup

  1. customA white precipitate was formed
  2. filtrationwhich was filtered
  3. customdried

Sources & evidence

ORD record
ord-36bef4e32d814f02bc9f655f3efd94be
Source dataset
uspto-grants-2012_11
Patent number
US08318740B2

Reaction notes

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