4-Bromo-2-methylaniline → 4'-Chloro-3-methylbiphen-4-ylamine

HRID 341679

반응식

HRID 341679 반응식
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=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:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:3]=[C:4]([CH3:9])[C:5]([NH2:6])=[CH:7][CH:8]=2)=[CH:13][CH:12]=1

참가 물질

7

반응물 3

HCID 114234-Bromo-2-methylanilineHCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acid

생성물 1

HCID 230051884'-Chloro-3-methylbiphen-4-ylamine수율 70.8%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

To a stirred, degassed solution of 4-bromo-2-methylaniline (20 g, 0.107 mol) in toluene (1200 ml) and ethanol (400 ml), under an atmosphere of nitrogen, is added 4-chlorophenylboronic acid (20.32 g, 0.13 mol) and the reaction mixture is stirred and heated to 80° C. Tetrakis(triphenylphosphine)palladium(0) (2.48 g, 0.002 mol) is added to the reaction mixture, and to this is added 2M aqueous potassium carbonate solution (160 ml). The reaction mixture is refluxed 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 extracts are combined and concentrated under reduced pressure to give 4′-chloro-3-methylbiphen-4-ylamine (16.5 g).

후처리

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. temperaturecooled to room temperature
  3. filtrationThe reaction mixture 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

출처 및 근거

ORD 기록
ord-9448fec464d840f59506ae2b53885044
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895761B2

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