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

HRID 1845355Notes

Reaction equation

HRID 1845355 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 7d, 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. filtrationthe precipitate was filtered
  4. washwashed with water affording the title compound (3 g, quant.) as a yellow powder

Sources & evidence

ORD record
ord-2a442df3452c443abf686b96679b5206
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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