Sodium Carbonate → 5-(4-Chlorophenyl)-2-methylaniline

HRID 72245

반응식

HRID 72245 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:13]=[CH:14][C:15]([CH3:19])=[C:16]([CH:18]=1)[NH2:17].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.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>[NH2:17][C:16]1[CH:18]=[C:12]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:13]=[CH:14][C:15]=1[CH3:19]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 27348055-Bromo-o-toluidine

생성물 1

HCID 233905465-(4-Chlorophenyl)-2-methylaniline수율 96.5%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
20 °C

실험 절차

Tetrakis(triphenylphosphine)palladium (0) (3.7 g, 0.003 mol) and 4-chlorophenylboronic acid (20.2 g, 0.13 mol) are added to a solution of 5-bromo-2-methylaniline (20 g, 0.1 mol) in 1,2-dimethoxyethane (200 ml). After stirring the reaction mixture for 15 minutes at 20° C., a solution of 20% aqueous sodium carbonate (300 ml) is added to the mixture, and the resulting mixture is heated at reflux for 24 hours. The reaction mixture is cooled to room temperature, diluted with water (600 ml) and extracted using ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and the filtrate evaporated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with 7% ethyl acetate in hexane to give 3-amino-4′-chloro-4-methylbiphenyl (21.0 g).

후처리

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux for 24 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. extractionextracted
  5. dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo
  8. customThe residue is further purified by column chromatography on silica gel
  9. washeluting with 7% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-e21403b9ac7543eabf75bf5ff62f0a7a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828908B2

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