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

HRID 71334

反応式

HRID 71334 の反応式
[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]

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 111373-NitrophenolHCID 11430Potassium Carbonate

生成物 1

HCID 308938Ethyl 2-(4-nitrophenoxy)acetate収率 92%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4eb61bebf99d4a4e982f90071ee3170f
出典データセット
uspto-grants-2014_09
特許番号
US08822685B2

関連ノート

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