2,3-Dinitrophenol → Ethyl 2-(2,3-dinitrophenoxy)acetate

HRID 415096

반응식

HRID 415096 반응식
[N+:1]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:13])([O-:3])=[O:2].Br[CH2:15][C:16]([O:18][C:19](C)(C)[CH3:20])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[N+:1]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[O:13][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 61912,3-DinitrophenolHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetate

생성물 1

HCID 86642030Ethyl 2-(2,3-dinitrophenoxy)acetate수율 70%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A round-bottom flask was charged with 2,3-dinitrophenol (11.04 g, 60 mmol, commercially available from Fluka-Sigma-Aldrich), tert-butyl bromoacetate (14.05 g, 66 mmol), acetonitrile (120 mL) and cesium carbonate (21.6 g). The mixture was stirred at room temperature overnight. The mixture was filtered, and the recovered solid was washed with ethyl acetate. The filtrate was further diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and combined organic solvent was washed with saturated brine, dried and concentrated under reduced pressure. The residue was triturated with ether to give ethyl 2-(2,3-dinitrophenoxy)acetate (13.0 g, 70% yield). 1H-NMR (DMSO-d6) δ 7.84 (d, 2H), 7.42 (s, 1H), 4.90 (s, 2H), 1.40 (S, 9H).

후처리

  1. filtrationThe mixture was filtered
  2. washthe recovered solid was washed with ethyl acetate
  3. additionThe filtrate was further diluted with ethyl acetate and water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwas washed with saturated brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with ether

출처 및 근거

ORD 기록
ord-b12faa9f3aab45d38b7a14f8b7d45680
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088767B2

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