4-Bromoanisole → 2-(4-Methoxyphenyl)benzonitrile

HRID 1768932

반응식

HRID 1768932 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C([Li])CCC.Br[C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19]>O1CCCC1.CCCCCC.CCOCC.[Cl-].[Zn+2].[Cl-].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:18]([C:17]1[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=1[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)#[N:19]

참가 물질

9

반응물 3

HCID 77304-BromoanisoleHCID 162722-BromobenzonitrileHCID 178418339Butyllithium

생성물 1

HCID 13933732-(4-Methoxyphenyl)benzonitrile

시약·촉매·용매 5

HCID 3007855Zincchloride촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

To a solution of 4-bromoanisole (18.7 g, 0.1 mol) in anhydrous tetrahydrofuran (200 mL) at -78° C. was added a solution of n-butyl lithium (2.5M, 50 mL) in hexane. After stirring for 0.5 hours, a solution of the zinc chloride (1M, 100 mL) in ether was added. After the mixture was stirred for 1 hour at -78° C., tetrakis (triphenylphosphine) palladium (0.85 g, 0.73 mmol) and 2-bromobenzonitrile (18.2 g, 0.1 mol) were added. The reaction mixture was stirred at room temperature overnight, and then was concentrated in vacuo. The residue was partitioned between ethyl acetate (100 mL) and 1N hydrochloric acid (100 mL). The organic solution was washed with brine and dried over magnesium sulfate. Concentration in vacuo gave crude 4-(2-cyanophenyl)anisole, which was directly used for next reaction. The compound can be triturated with ether to obtain a pure solid product.

후처리

  1. stirringAfter the mixture was stirred for 1 hour at -78° C.
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. concentrationwas concentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate (100 mL) and 1N hydrochloric acid (100 mL)
  5. washThe organic solution was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationConcentration in vacuo

출처 및 근거

ORD 기록
ord-7842e73193204e33a44698038c9ab303
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05380719

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