Diethyl Ether → 1-Phenyl-2-methylbenzothiophenium triflate

HRID 432538ノート

反応式

HRID 432538 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 111324971-Phenyl-2-methylbenzothiophenium triflate収率 76%

試薬・触媒・溶媒 2

HCID 164650Cupric benzoate触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1d3098c42c4f473e98fc013543f933f0
出典データセット
uspto-grants-2003_12
特許番号
US06664022B1

反応ノート

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