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

HRID 1887235Notes

Reaction equation

HRID 1887235 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 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred solution of 3-thiophenecarboxylic acid (1.00 g, 7.80 mmol) in glacial acetic acid (9 mL) at ambient temperature under nitrogen atmosphere was slowly added bromine (0.39 mL, 7.53 mmol) in glacial acetic acid (6 mL). The reaction mixture was stirred for 15 minutes, then quenched with cold water (50 mL). The precipitate was filtered, washed with water and dried in vacuum oven at 50° C. to afford 5-bromo-3-thiophenecarboxylic acid as a colorless solid (0.78 g, 50%): mp 133-135° C.; 1H NMR (300 MHz, CDCl3) δ 8.12 (d, J=1.5 Hz, 1H), 7.51 (d, J=1.5 Hz, 1H).

Workup

  1. customat ambient temperature
  2. customquenched with cold water (50 mL)
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried in vacuum oven at 50° C.

Sources & evidence

ORD record
ord-050ba2491d684d03a6b5bea334fc5f6f
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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