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

HRID 1768932

反応式

HRID 1768932 の反応式
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]

参加物

9

反応物 3

HCID 77304-BromoanisoleHCID 162722-BromobenzonitrileHCID 178418339Butyllithium

生成物 1

HCID 13933732-(4-Methoxyphenyl)benzonitrile

試薬・触媒・溶媒 5

HCID 3007855Zincchloride触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7842e73193204e33a44698038c9ab303
出典データセット
uspto-grants-1995_01
特許番号
US05380719

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