Bromine → 1-(4-Bromothiophen-2-yl)-2-methylpropan-1-one

HRID 387343Notes

Reaction equation

HRID 387343 reaction equation
[CH3:1][CH:2]([CH3:10])[C:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[Br:15]Br>C(Cl)(Cl)Cl>[Br:15][C:8]1[CH:9]=[C:5]([C:3](=[O:4])[CH:2]([CH3:10])[CH3:1])[S:6][CH:7]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 38624802-Methyl-1-(thiophen-2-yl)propan-1-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 593327031-(4-Bromothiophen-2-yl)-2-methylpropan-1-oneYield 40%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-methyl-1-(2-thienyl)-1-propanone (2.3 g, 15 mmol) was diluted in chloroform (10 mL), and aluminum chloride (4.5 g, 34 mmol, 2.3 eq) was added. Bromine (0.82 mL, 16 mmol, 1.1 eq) was added as a solution in chloroform (15 mL), and the mixture was stirred at rt over the weekend. The crude reaction mixture was carefully poured onto ice water, then extracted with chloroform. The combined organics were dried over sodium sulfate, filtered, and concentrated to afford brown oil. The crude was purified by isco combiflash to give the title compound as brown oil (1.28 g, 40%).

Workup

  1. customThe crude reaction mixture
  2. additionwas carefully poured onto ice water
  3. extractionextracted with chloroform
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford brown oil
  8. customThe crude was purified by isco combiflash

Sources & evidence

ORD record
ord-0007e758cce94746b052f152241026e7
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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