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

HRID 2377250Notes

Reaction equation

HRID 2377250 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 acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Thiophene-3-carboxylic acid (5.0 g, 39.0 mmol) was dissolved in glacial acetic acid (40 mL) and a solution of bromine (1.9 mL, 37.9 mmol) in glacial acetic acid (25 mL) was added dropwise. After about 2 hours, the reaction mixture was poured into ice water (200 mL) and the formed precipitate was collected by filtration. The filter cake was washed with a minimal amount of ice water and was recrystallized from water to provide the desired product. MS (DCI-NH3): m/z 206, 208 (M)+.

Workup

  1. filtrationthe formed precipitate was collected by filtration
  2. washThe filter cake was washed with a minimal amount of ice water
  3. customwas recrystallized from water

Sources & evidence

ORD record
ord-d965bd6388f9474fb6d8ffbf9fcf443b
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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