Diethyl Ether → 1-Phenyl-2-methylbenzothiophenium triflate

HRID 432538

반응식

HRID 432538 반응식
[CH3:1][C:2]1[S:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[O-:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13].[C:19]1([I+]C2C=CC=CC=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)C>O.C([O-])(=O)C1C=CC=CC=1.[Cu+2].C([O-])(=O)C1C=CC=CC=1>[O-:14][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:13])=[O:11].[C:19]1([S+:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[CH:3]=[C:2]2[CH3:1])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

6

반응물 3

HCID 3283Diethyl EtherHCID 709522-Methylbenzo(b)thiopheneHCID 2737137Diphenyliodonium trifluoromethanesulfonate

생성물 1

HCID 111324971-Phenyl-2-methylbenzothiophenium triflate수율 76%

시약·촉매·용매 2

HCID 164650Cupric benzoate촉매HCID 962Water용매

실험 절차

2-Methylthianaphthene (5 g, 0.0327 mole), diphenyliodonium triflate (18.28 g, 0.0425 mole) and copper benzoate (0.1 g, 0.000327 mole) were heated without solvent for 0.5 hours at 140° C. under a nitrogen atmosphere. After cooling down, 150 ethyl ether was added to solidify the product. Filtration and washing with ethyl ether yielded a brownish-grey solid, which was dissolved in 500 ml hot water, and the solution filtered and the water removed in vacuo. The resulting off-white solid was stirred in 50 ml ethyl ether for 1 hour, the mixture filtered and the residue washed with ethyl ether. The product was recrystallized from dichloromethane/t-butyl methyl ether to yield 8.97 g (76%) of 1-phenyl-2-methylbenzothiophenium triflate. The structure was confirmed by 1H/13C NMR spectroscopy.

후처리

  1. temperatureAfter cooling down
  2. filtrationFiltration
  3. washwashing with ethyl ether
  4. customyielded a brownish-grey solid, which
  5. filtrationthe solution filtered
  6. customthe water removed in vacuo
  7. filtrationthe mixture filtered
  8. washthe residue washed with ethyl ether
  9. customThe product was recrystallized from dichloromethane/t-butyl methyl ether

출처 및 근거

ORD 기록
ord-1d3098c42c4f473e98fc013543f933f0
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664022B1

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