Ethyl bromoacetate → Ethyl 2-(4-nitrophenoxy)acetate

HRID 76444

반응식

HRID 76444 반응식
[N+:1]([C:4]1[CH:5]=[C:6](O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C([O-])([O-])=[O:12].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CC(C)=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:12][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:8][CH:9]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 111373-NitrophenolHCID 11430Potassium Carbonate

생성물 1

HCID 308938Ethyl 2-(4-nitrophenoxy)acetate수율 92%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A dry reaction flask equipped with a reflux condenser, N2 inlet and a magnetic stirring bar was charged with 3-nitrophenol (76.45 g, 550 mmol), K2CO3 (76.45 g, 550 mmol) and dry acetone (500 mL) under N2 atmosphere. To this at room temperature was added ethyl bromoacetate (55.44 mL, 500 mmol) over a period of 15 min. The reaction mixture was refluxed for 16 h, cooled and poured over ice-water (4 Kg). The resulting aqueous solution was extracted with CH2Cl2 (3×500 mL), dried over anhydrous Na2SO4 and solvent was removed to obtain 103 g (92%) of the desired ethyl 4-nitrophenoxyacetate. 1H NMR (CDCl3): δ 8.20 (d, 2H, J=8.2 Hz), 6.95 (d, 2H, J=8.1 Hz), 4.72 (s, 2H), 4.25 (q, 2H), 1.23 (t, 3H); LCMS: ret. time: 27.07 min.; purity: 100%; MS: 267 (M+ acetonitrile).

후처리

  1. customA dry reaction flask
  2. customequipped with a reflux condenser, N2 inlet and a magnetic stirring bar
  3. temperatureThe reaction mixture was refluxed for 16 h
  4. temperaturecooled
  5. extractionThe resulting aqueous solution was extracted with CH2Cl2 (3×500 mL)
  6. dry with materialdried over anhydrous Na2SO4 and solvent
  7. customwas removed

출처 및 근거

ORD 기록
ord-dad13508e6ca44339f09af30f9df7450
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835430B2

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