Potassium Carbonate → N-(4'-chloro-3-ethylbiphen-4-yl)acetamide

HRID 72288

반응식

HRID 72288 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH2:12][CH3:13])[CH:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:3]=[C:4]([CH2:12][CH3:13])[C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 2735223N-(4-bromo-2-ethylphenyl)acetamide

생성물 1

HCID 59450487N-(4'-chloro-3-ethylbiphen-4-yl)acetamide수율 91.3%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

To a degassed solution of N-(4-bromo-2-ethylphenyl)acetamide (20 g, 0.082 mol) in toluene (1200 ml) and ethanol (400 ml), 4-chlorobenzene boronic acid (15.5 g, 0.099 mol) is added under an atmosphere of nitrogen, and the reaction mixture is heated to 80° C. Tetrakis(triphenylphosphine)palladium(0) (2.0 g, 0.0017 mol) is added followed by 2M aqueous potassium carbonate solution (160 ml). The reaction mixture is heated at reflux for 4 hours then cooled to room temperature. The reaction mixture is filtered through diatomaceous earth, and the filtrate is evaporated under reduced pressure. The residue is partitioned between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate (3×500 ml) and the organic solutions are combined and concentrated under reduced pressure to give N-(4′-chloro-3-ethylbiphen-4-yl)acetamide (20.5 g).

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 4 hours
  3. temperaturethen cooled to room temperature
  4. filtrationThe reaction mixture is filtered through diatomaceous earth
  5. customthe filtrate is evaporated under reduced pressure
  6. customThe residue is partitioned between ethyl acetate and water
  7. extractionThe aqueous phase is extracted with ethyl acetate (3×500 ml)
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a0c1abc68792466d9fe31d229cb7b1a5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828908B2

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