Hydrochloric Acid → p-[(Trifluorovinyl)dimethylsilyl]phenetole

HRID 726520

反応式

HRID 726520 の反応式
Br[C:2]([F:6])=[C:3]([F:5])[F:4].Cl[Si:8]([CH3:19])([CH3:18])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=1.C([Li])(CC)C.C1CCCCC1.Cl>CCOCC>[F:6][C:2]([Si:8]([CH3:18])([CH3:19])[C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH3:17])=[CH:13][CH:14]=1)=[C:3]([F:5])[F:4]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 8078CyclohexaneHCID 117301-Bromo-1,2,2-trifluoroetheneHCID 14014482Chloro(4-ethoxyphenyl)dimethylsilaneHCID 178418400CID 53628100

生成物 1

HCID 19706492p-[(Trifluorovinyl)dimethylsilyl]phenetole収率 66.9%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
-65 °C

実験手順

A -30° C. solution of bromotrifluoroethylene (7.15 g, 0.044 mol) in ether is treated with p-(chlorodimethylsilyl)phenetole (9.54 g, 0.044 mol), cooled to -65° C., treated dropwise with a 1.3M solution of sec-butyllithium in cyclohexane (34.2 mL, 0.044 mol) while maintaining the temperature below -60° C., stirred at -65° C. for 5 hours, stirred at room temperature overnight, cooled to 0° C., treated with dilute hydrochloric acid, and diluted with ether. The organic phase is separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a residue which is distilled to give the title product as a clear liquid (7.66 g, bp 84°-92° C./0.8 mm Hg).

後処理

  1. temperaturewhile maintaining the temperature below -60° C.
  2. stirringstirred at room temperature overnight
  3. temperaturecooled to 0° C.
  4. customThe organic phase is separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain a residue which
  9. distillationis distilled

出典と根拠

ORDレコード
ord-3bc9fb260f91463c93e8c4ad1090e966
出典データセット
uspto-grants-1998_01
特許番号
US05710102

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