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

HRID 1960984Notes

Reaction equation

HRID 1960984 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-2cab48b78f89412a911669c48cca3441
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

Loading…