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

HRID 2391950Notes

Reaction equation

HRID 2391950 reaction equation
[Br:1]Br.[CH3:3][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[CH3:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 747135-Methylthiophene-2-carboxylic acid

Product 1

HCID 8188894-Bromo-5-methylthiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (725 uL, 14.1 mmol) in AcOH (2.8 mL) was added dropwise to 5-methyl-2-thiophenecarboxylic acid (2 g, 14.1 mmol) and FeCl3 (456 mg, 2.81 mmol) in AcOH (28 mL) at 25° C. After 5 h, 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 222 (M+H)+.

Workup

  1. additionthe solution was poured onto ice
  2. filtrationthe precipitate was filtered
  3. washwashed with water affording the title compound (3 g, quant.) as a yellow powder

Sources & evidence

ORD record
ord-241819749b534e4fba49cab39aa5ffc4
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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