Bromine → 4-Bromo-5-chlorothiophene-2-carboxylic acid

HRID 2391952Notes

Reaction equation

HRID 2391952 reaction equation
[Br:1]Br.[Cl:3][C:4]1[S:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1>CC(O)=O>[Br:1][C:5]1[CH:6]=[C:7]([C:9]([OH:11])=[O:10])[S:8][C:4]=1[Cl:3]

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 950485-Chloro-2-thiophenecarboxylic acid

Product 1

HCID 148824034-Bromo-5-chlorothiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (634 uL, 12.3 mmol) in AcOH (2.5 mL) was added dropwise to 5-chloro-2-thiophenecarboxylic acid (2 g, 12.3 mmol) and FeCl3 (399 mg, 2.50 mmol) in AcOH (25 mL) at 25° C. The reaction mixture was warmed to reflux where additional bromine (634 uL, 12.3 mmol) and FeCl3 (399 mg, 2.50 mmol) were added. After 7 d, the solution was poured onto ice and the precipitate was filtered and washed with water affording the title compound (3 g, quant.) as a yellow powder: LCMS (ES) m/z 242 (M+H)+.

Workup

  1. temperatureThe reaction mixture was warmed
  2. additionwere added
  3. additionthe solution was poured onto ice
  4. filtrationthe precipitate was filtered
  5. washwashed with water affording the title compound (3 g, quant.) as a yellow powder

Sources & evidence

ORD record
ord-0f386649c65943b89eb81d7c11c5194f
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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