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

HRID 1726340Notes

Reaction equation

HRID 1726340 reaction equation
[Br:1]Br.[S:3]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4]1>C(O)(=O)C>[Br:1][C:7]1[S:3][CH:4]=[C:5]([C:8]([OH:10])=[O:9])[CH:6]=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

Bromine (46.5 g) in acetic acid (200 mL) was added dropwise to a solution of thiophene-3-carboxylic acid (38 g) in acetic acid (300 mL). After the addition was complete, stirring was continued at room temperature for 30 min. The reaction mixture was poured into 2000 mL of ice/water and the precipitated solid was collected and recrystallised from water to give a colourless solid; MS (ES−) 205, 207 (MH+).

Workup

  1. additionAfter the addition
  2. customthe precipitated solid was collected
  3. customrecrystallised from water
  4. customto give a colourless solid

Sources & evidence

ORD record
ord-2997701d2b6e4370931baf1912c77b51
Source dataset
uspto-grants-2009_02
Patent number
US07491734B2

Reaction notes

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