Tetrahydrofuran → (1,1'-Biphenyl)-4-carbonitrile

HRID 13875

반응식

HRID 13875 반응식
O1CCCC1.[C:6]1([Mg]Cl)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1.[Cl-].[NH4+]>[Cl-].[Zn+2].[Cl-].C1(C)C=CC=CC=1.CN1CCCC1=O>[C:19]([C:18]1[CH:21]=[CH:22][C:15]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:16][CH:17]=1)#[N:20]

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 121634-ChlorobenzonitrileHCID 25517Ammonium ChlorideHCID 178478979HCID 178478979, 화합물

생성물 1

HCID 18021(1,1'-Biphenyl)-4-carbonitrile

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 1140Toluene용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

A 50-ml four-necked flask was equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser. 1.090 g (8 mmol) of zinc chloride and 4 ml of N-methylpyrrolidinone were weighed in the flask. The flask was purged with argon, followed by stirring. 3.4 ml (7.5 mmol) of 2.2M tetrahydrofuran solution of phenylmagnesium chloride was added dropwise at 25° C. over a period of 30 minutes, followed by stirring at 25° C. for 30 minutes. The reaction liquid previously obtained was added, followed by stirring at 25° C. for 30 minutes. Further, 0.688 g (5 mmol) of 4-chlorobenzonitrile was added, followed by stirring at 120° C. for 9 hours. After the completion of the reaction, 10 ml of toluene and 10 ml of saturated aqueous ammonium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 0.670 g of 4-cyanobiphenyl (yield: 75 mol % based on 4-chlorobenzonitrile). The identification of the product was made by mass spectroscopy.

후처리

  1. customA 50-ml four-necked flask was equipped with a stirrer
  2. customThe flask was purged with argon
  3. stirringby stirring at 25° C. for 30 minutes
  4. customThe reaction liquid
  5. custompreviously obtained
  6. additionwas added
  7. stirringby stirring at 25° C. for 30 minutes
  8. stirringby stirring at 120° C. for 9 hours
  9. additionwere added
  10. customfollowed by separation
  11. customThe organic phase was purified by column chromatography

출처 및 근거

ORD 기록
ord-72efa29d38e04fa1a93f6dd0799df980
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728176B2

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