N-methyl-2-pyrrolidone → Benzo[b]thiophene, 7-methyl-3-(trifluoromethyl)-

HRID 649008Notes

Reaction equation

HRID 649008 reaction equation
Br[C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:4]=2[S:5][CH:6]=1.[C:12](C(O[Na])=O)([F:15])([F:14])[F:13].CN1CCCC1=O>[Cu]I.O>[CH3:11][C:7]1[C:4]2[S:5][CH:6]=[C:2]([C:12]([F:15])([F:14])[F:13])[C:3]=2[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 6150893-Bromo-7-methyl-1-benzothiopheneHCID 178526070HCID 178526070, compound

Product 1

HCID 14780494Benzo[b]thiophene, 7-methyl-3-(trifluoromethyl)-

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Procedure

A mixture of 2 g of 3-bromo-7-methylbenzo[b]thiophene, 4.8 g of CF3COONa, 3 g CuI and 20 ml of 1-methylpyrrolidone are vigorously stirred and heated at 160°. After a short while evolution of gas commences. Stirring is continued for one hour at 160° and a further hour at 180°. After cooling the reaction mixture is poured into water, extracted with ether/hexane (1/1) and the organic phase washed, dried and concentrated under vacuum. The raw product is chromatographed over silica gel (eluant: n-hexane) and the title compound obtained as a colourless oil.

Workup

  1. temperatureheated at 160°
  2. stirringStirring
  3. temperatureAfter cooling the reaction mixture
  4. extractionextracted with ether/hexane (1/1)
  5. washthe organic phase washed
  6. customdried
  7. concentrationconcentrated under vacuum
  8. customThe raw product is chromatographed over silica gel (eluant: n-hexane)

Sources & evidence

ORD record
ord-bbe69fa6f3ad4b2196c1877af77c7483
Source dataset
uspto-grants-1988_04
Patent number
US04737516

Reaction notes

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