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

HRID 378090Notes

Reaction equation

HRID 378090 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 63.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 3-thiophenecarboxylic acid (7.7 g, 60 mmol) in 70 mL acetic acid was added a solution of 9.6 g bromine in 50 mL acetic acid at RT and stirring was continued at RT for 0.5 h. After that, the reaction mixture was poured into 600 mL ice-water. The precipitate was filtered, washed with water and air-dried to give 7.9 g of 5-bromo-3-thiophenecarboxylic acid.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customair-dried

Sources & evidence

ORD record
ord-cf51ee844a6e485d9b9dec943b355454
Source dataset
uspto-grants-2000_02
Patent number
US06028101

Reaction notes

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