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

HRID 43327노트

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HRID 43327 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]([CH2:19][CH3:20])=[C:16]([CH:18]=1)[NH2:17].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:13]=[CH:14][C:15]([CH2:19][CH3:20])=[C:16]([CH:18]=2)[NH2:17])=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 233467565-Bromo-2-ethylaniline

생성물 1

HCID 594459455-(4-Chlorophenyl)-2-ethylaniline수율 88.2%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
20 °C

실험 절차

4-Chlorophenylboronic acid (13.2 g, 0.08 mol) and tetrakis(triphenylphosphine) palladium (0) (2.4 g, 0.002 mol) are added to a solution of 5-bromo-2-ethylaniline (14.1 g, 0.07 mol) in 1,2-dimethoxyethane (140 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 refluxed for 24 hours. The reaction mixture is cooled to room temperature, diluted with water 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 5% ethyl acetate in hexane to give 5-(4-chlorophenyl)-2-ethylaniline (14.3 g).

후처리

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

출처 및 근거

ORD 기록
ord-9dc7fad2288147edbc64788618dc9274
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536351B2

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