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

HRID 415096

反応式

HRID 415096 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b12faa9f3aab45d38b7a14f8b7d45680
出典データセット
uspto-grants-2012_01
特許番号
US08088767B2

関連ノート

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