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

HRID 720232Notes

Reaction equation

HRID 720232 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1.[Br:9]Br>CC(O)=O>[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 acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of thiophene-3-carboxylic acid (25 g, 195 mmol) in AcOH (700 ml) was added bromine (10.6 ml) in AcOH (200 ml) dropwise. After the addition, the reaction was stirred for 30 minutes at room temperature and poured onto water. A white precipitate was formed, which was filtered and dried to obtain 5-bromo-thiophene-3-carboxylic acid (14.5 g) as a white solid after crystallization (water).

Workup

  1. additionAfter the addition
  2. additionpoured onto water
  3. customA white precipitate was formed
  4. filtrationwhich was filtered
  5. customdried

Sources & evidence

ORD record
ord-6c30602e308e4baaac6aaaabc7ae7174
Source dataset
uspto-grants-2006_11
Patent number
US07135470B2

Reaction notes

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