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

HRID 422033

반응식

HRID 422033 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

반응 조건

온도
110 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-aa490170718c48e58721ae2e7a7b0cfe
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101608B2

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