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

HRID 656105Notes

Reaction equation

HRID 656105 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-6e82853107d04ec6ae5b57c01e3c76bc
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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