Cesium carbonate → N-ethyl-5-(furan-3-yl)-2-methylaniline

HRID 1964015

반응식

HRID 1964015 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[NH:7][CH2:8][CH3:9].[O:12]1[CH:16]=[CH:15][C:14](B2OC(C)(C)C(C)(C)O2)=[CH:13]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[CH2:8]([NH:7][C:6]1[CH:10]=[C:2]([C:14]2[CH:15]=[CH:16][O:12][CH:13]=2)[CH:3]=[CH:4][C:5]=1[CH3:11])[CH3:9]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 27739962-(Furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 437296995-bromo-N-ethyl-2-methylaniline

생성물 1

HCID 66877311N-ethyl-5-(furan-3-yl)-2-methylaniline수율 98%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

0.69 g (3.20 mmol) of 5-bromo-N-ethyl-2-methylaniline and 0.93 g (4.80 mmol) of 3-furan boronic acid pinacol ester were dissolved in 7 mL of THF. 1.56 g (4.80 mmol) of cesium carbonate and 370 mg (0.32 mmol) of tetrakis(triphenyl phosphine)palladium(0) were added thereto and heated under reflux for 22 hours. After completion of the reaction, filtration was conducted, and the filtrate was condensed. The resulting crude product was separated and purified using silica gel column chromatography to give N-ethyl-5-(furan-3-yl)-2-methylaniline (yield: 98%).

후처리

  1. temperatureheated
  2. temperatureunder reflux for 22 hours
  3. customAfter completion of the reaction, filtration
  4. customcondensed
  5. customThe resulting crude product was separated
  6. custompurified

출처 및 근거

ORD 기록
ord-6f317208b33b4f2a8539517b604f631b
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415479B2

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