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

HRID 341684

反応式

HRID 341684 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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 refluxed for 4 hours then cooled to room temperature. The reaction mass 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).

後処理

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

出典と根拠

ORDレコード
ord-5388bc0b48604eeaa7b66a6db5dc15f4
出典データセット
uspto-grants-2014_11
特許番号
US08895761B2

関連ノート

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