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

HRID 557618

반응식

HRID 557618 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 666605281-(Biphenyl-4-YL)-cyclopropanecarbonitrile수율 99.4%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
65 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-0b724cd5e16b465b81f0a7b601e04b9c
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058300B2

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