Isopropanol → 1-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrile

HRID 35694

反応式

HRID 35694 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[CH2:5][C:6]#[N:7].Br[CH2:13][CH2:14][CH2:15]Br.[H-].[Na+].CC(O)C>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2([C:6]#[N:7])[CH2:15][CH2:14][CH2:13]2)[CH:8]=[CH:9][C:10]=1[Cl:11]

参加物

7

反応物 4

HCID 3776IsopropanolHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 76690(3,4-Dichlorophenyl)acetonitrile

生成物 1

HCID 108571341-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrile

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 962Water溶媒

実験手順

A solution of 3,4-dichlorobenzyl cyanide (25 g) and 1,3-dibromopropane (15 ml) in dry dimethyl sulphoxide (150 ml) was added dropwise under nitrogen to a stirred mixture of sodium hydride (7.5 g) dispersed in mineral oil (7.5 g) and dimethylsulphoxide (200 ml) at a temperature in the range 30° to 35° C. The mixture was stirred at room temperature for two hours and propan-2-ol (8 ml) and then water (110 ml) were added dropwise. The mixture was filtered through a diatomaceous earth sold under the Registered Trade Mark CELITE and the solid residue washed with ether. The ether layer was separated, washed with water, dried and evaporated. 1-(3,4-Dichlorophenyl)-1-cyclobutanecarbonitrile (b.p. 108°-120° C. at 0.15 Hg) was isolated by distillation. This method is a modification of that described by Butler and Pollatz (J. Org. Chem., Vol. 36, No. 9, 1971, p. 1308).

後処理

  1. filtrationThe mixture was filtered through a diatomaceous earth
  2. washthe solid residue washed with ether
  3. customThe ether layer was separated
  4. washwashed with water
  5. customdried
  6. customevaporated

出典と根拠

ORDレコード
ord-076b3e72c334497387329e955d8a4dbf
出典データセット
uspto-grants-1988_08
特許番号
US04767790

関連ノート

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