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

HRID 238275Notes

Reaction equation

HRID 238275 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 33.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Thiophene-3-carboxylic acid (25 g, 195 mmol) was dissolved in acetic acid (200 mL). Bromine (10.4 mL, 200 mmol) was added slowly over the course of 0.5 hour. The mixture was stirred for a further 0.5 hour and then poured onto ice. After 0.5 hours the white precipitate that formed was collected by filtration. Recrystallisation from water gave the title compound as a white solid (13.7 g). 1H NMR (400 MHz, d6-DMSO): δ 8.25 (s, 1H), 7.45 (s, 1H).

Workup

  1. additionpoured onto ice
  2. customAfter 0.5 hours the white precipitate that formed
  3. filtrationwas collected by filtration
  4. customRecrystallisation from water

Sources & evidence

ORD record
ord-59a31fbfff5743b1b78988d000a21003
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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