Acetic Acid → Ethyl (4-bromo-2-nitrophenyl)acetate

HRID 422033

反応式

HRID 422033 の反応式
[CH3:1][O:2][C:3](=[O:19])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])C(OC)=O.Cl.[C:21](O)(=O)C>>[CH2:1]([O:2][C:3](=[O:19])[CH2:4][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])[CH3:21]

参加物

4

反応物 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 157405961,3-Dimethyl 2-(4-bromo-2-nitrophenyl)propanedioate

生成物 1

HCID 23247724Ethyl (4-bromo-2-nitrophenyl)acetate

反応条件

温度
110 °C

実験手順

To a suspension of 2-(4-bromo-2-nitro-phenyl)-malonic acid dimethyl ester (crude, 8.1 mmol) in acetic acid (10 mL) is added 6N HCl (10 mL). The mixture is heated at 110° C. overnight (about 15 hr). The reaction mixture is evaporated to dryness. The crude is used in the next step without further purification. To a solution of the crude in ethanol (40 mL) is added concentrated H2SO4 (3 drops) and the resulting reaction mixture is heated at reflux over night. Solvent is removed under reduced pressure. It is purified by flash column chromatography. 1H NMR (400 MHz, CDCl3) δ 8.25 (s, 1 H), 7.72-7.7 (m, 1 H), 7.26-7.22 (m, 1 H), 4.23-4.13 (q, 2 H), 3.97 (s, 2 H), 1.29-1.23 (t, 3 H).

後処理

  1. customThe reaction mixture is evaporated to dryness
  2. customThe crude is used in the next step without further purification
  3. additionTo a solution of the crude in ethanol (40 mL) is added concentrated H2SO4 (3 drops)
  4. customthe resulting reaction mixture
  5. temperatureis heated
  6. temperatureat reflux over night
  7. customSolvent is removed under reduced pressure
  8. customIt is purified by flash column chromatography

出典と根拠

ORDレコード
ord-aa490170718c48e58721ae2e7a7b0cfe
出典データセット
uspto-grants-2012_01
特許番号
US08101608B2

関連ノート

読み込み中…