Iodine → 6,7-Dichloro-4-formylquinoline

HRID 599357

反応式

HRID 599357 の反応式
F[C:2](F)(F)[C:3]([OH:5])=O.C(I)(C)(C)C.II.[Cl:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[Cl:26])[N:22]=[CH:21][CH:20]=C2C.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>CS(C)=O.O.O.O.O.[Fe](Cl)Cl.C(OCC)(=O)C>[Cl:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[Cl:26])[N:22]=[CH:21][CH:20]=[C:2]2[CH:3]=[O:5]

参加物

10

反応物 6

HCID 807IodineHCID 6422Trifluoroacetic acidHCID 112062-Iodo-2-methylpropaneHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 219928806,7-Dichloro-4-methylquinoline

生成物 1

HCID 866180056,7-Dichloro-4-formylquinoline収率 99%

試薬・触媒・溶媒 3

HCID 16211588Ferrous chloride tetrahydrate触媒HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Trifluoroacetic acid (360 μL, 4.7 mmol), tert-butyl iodide (450 μL, 3.8 mmol), iodine (990 mg, 3.9 mmol) and iron(II) chloride tetrahydrate (170 mg, 0.85 mmol) were added sequentially to a solution of 6,7-dichloro-4-methylquinoline (Reference compound No. 1-2, 790 mg, 3.7 mmol) in dimethylsulfoxide (18 mL) at room temperature, and the mixture was stirred at 80° C. for 7 hours. Then saturated sodium thiosulfate aqueous solution (100 mL) was added, and then ethyl acetate (300 mL) and saturated aqueous sodium hydrogencarbonate solution (200 mL) were added thereto. The mixture was separated into the organic layer and the aqueous layer, and the organic layer was washed with saturated brine (100 mL), dried over anhydrous magnesium sulfate, The solvent was evaporated under reduced pressure to give 840 mg of the title reference compound as a brown solid (Yield: 99%).

後処理

  1. customThe mixture was separated into the organic layer
  2. washthe aqueous layer, and the organic layer was washed with saturated brine (100 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-ef43c900f8c9448a885bb5d4533180fa
出典データセット
uspto-grants-2011_03
特許番号
US07897774B2

関連ノート

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