Potassium Carbonate → HCID 22057729、化合物

HRID 1828710ノート

反応式

HRID 1828710 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][CH3:11].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:10]([C:3]1[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:2]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:11]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 66827Phenylboronic AcidHCID 220577304-Bromo-3-ethylbenzonitrile

生成物 1

HCID 22057729HCID 22057729、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

A mixture of 4-bromo-3-ethyl benzonitrile (1 g, 4.76 mmol), phenylboronic acid (1.16 g, 9.5 mmol), K2CO3 (1.97 g, 14.3 mmol), and Pd(PPh3)4 (543 mg, 0.48 mmol) in DMF (anhydrous, 15 mL) is heated in a sealed tube at 120° C. for 12 h. After cooling to room temperature, the reaction mixture is poured into a mixture of ice and saturated aqueous NH4Cl. The mixture is extracted with EtOAc (3×30 mL). The combined organic layers are washed with saturated aqueous NaCl, dried over Na2SO4, and concentrated. The crude product obtained is purified by silica gel chromatography (5% EtOAc in hexanes) to give 2-ethyl-biphenyl-4-carbonitrile as a colorless oil.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionThe mixture is extracted with EtOAc (3×30 mL)
  3. washThe combined organic layers are washed with saturated aqueous NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product obtained
  7. customis purified by silica gel chromatography (5% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-ffd18a6920074f0c918ea703a843d42d
出典データセット
uspto-grants-2006_06
特許番号
US07060697B2

反応ノート

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