1,2-Dibromoethane → 1-(Biphenyl-4-YL)-cyclopropanecarbonitrile

HRID 557618

反応式

HRID 557618 の反応式
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]#[N:15])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Br[CH2:19][CH2:20]Br.CCOC(C)=O>O.C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:12]=[CH:11][C:10]([C:13]2([C:14]#[N:15])[CH2:20][CH2:19]2)=[CH:9][CH:8]=1

参加物

8

反応物 4

HCID 78391,2-DibromoethaneHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 358564-Biphenylacetonitrile

生成物 1

HCID 666605281-(Biphenyl-4-YL)-cyclopropanecarbonitrile収率 99.4%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
65 °C

実験手順

4-phenyl-phenylacetonitrile (VWR scientific, 55.7 g, 289 mmol) was added to a solution of KOH (161.6 g, 2890 mmol) in water (170 mL) and toluene (550 mL) at room temperature. Tetrabutyl ammonium bromide (9.2 g, 29 mmol) followed by 1,2 dibromoethane (64.9 g, 347 mmol) were added and the solution was heated to 65° C. overnight. Reaction complete by TLC (10% EtOAc/hex). The organic layer was extracted 2 times with dilute hydrochloric acid, dried and evaporated to yield 63 g of 1-(biphenyl-4-yl)cyclopropanecarbonitrile.

後処理

  1. additionwere added
  2. extractionThe organic layer was extracted 2 times with dilute hydrochloric acid
  3. customdried
  4. customevaporated

出典と根拠

ORDレコード
ord-0b724cd5e16b465b81f0a7b601e04b9c
出典データセット
uspto-grants-2011_11
特許番号
US08058300B2

関連ノート

読み込み中…