Hydrogen Bromide → 5-Bromothiophene-3-carboxylic acid

HRID 1771925Notes

Reaction equation

HRID 1771925 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-47026f3ddbd74f558f7d3ac670e56252
Source dataset
uspto-grants-2016_02
Patent number
US09249154B2

Reaction notes

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