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

HRID 357735Notes

Reaction equation

HRID 357735 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1.C1C=C[NH+]=CC=1.[Br:15][Br-]Br>C(O)(=O)C>[Br:15][C:5]1[S:1][CH:2]=[C:3]([C:6]([OH:8])=[O:7])[CH:4]=1

Participants

3

Reactant 1

HCID 6918Thiophene-3-carboxylic acid

Product 1

HCID 120399785-Bromothiophene-3-carboxylic acidYield 95.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 3-thiophenecarboxylic acid (12.81 g), pyridinium bromide perbromide (35.54 g) and acetic acid (50 ml) was stirred at 45° C. for 48 hours. The mixture was poured into ice-water and precipitated crystals were collected by filtration. The crystals were dissolved in ethyl acetate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 5-bromo-3-thiophenecarboxylic acid (19.78 g) as crystals.

Workup

  1. customprecipitated crystals
  2. filtrationwere collected by filtration
  3. dissolutionThe crystals were dissolved in ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e0f33865263b40a3a8a8eb6eb3697abc
Source dataset
uspto-grants-1998_11
Patent number
US05840917

Reaction notes

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