Ethyl Lactate → Ethyl 2-(5-fluoro-2-nitrophenoxy)propanoate

HRID 128483

반응식

HRID 128483 반응식
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]([O:17][CH2:18][CH3:19])(=[O:16])[CH:13]([CH3:15])[OH:14].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([CH:7]=1)[O:14][CH:13]([CH3:15])[C:12]([O:17][CH2:18][CH3:19])=[O:16]

참가 물질

5

반응물 3

HCID 7344Ethyl LactateHCID 11430Potassium CarbonateHCID 679672,4-Difluoronitrobenzene

생성물 1

HCID 19786322Ethyl 2-(5-fluoro-2-nitrophenoxy)propanoate

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
95 °C

실험 절차

2,4-Difluoronitrobenzene (16.9 g; 0.10 mole), ethyl lactate (11.8 g; 0.10 mole), and anhydrous potassium carbonate (13.8 g, 0.10 mole) are combined in dioxane (200 ml) and the temperature is brought to 95° C. over a 1.5 hour period and maintained at 95° C. for 3 hours. The reaction mixture is cooled to room temperature, the inorganic solids removed by filtration and the solvent removed under vacuum to afford a dark colored oil, from which low boiling fractions are removed by distillation (bp., 79° C./0.5 mm). The pot residue is then cooled to afford 15.9 g of crude product, which is recrystallized from ligroin/acetone to afford ethyl 2-(5-fluoro-2-nitrophenoxy)propionate as yellow needles, m.p. 64°-65° C. Elemental anal. Calcd for C11H12FNO5 : C, 51.4; H, 4.70; F, 7.38; N, 5.45. Found: C, 51.35; H, 4.74; F, 7.60; N, 5.44.

후처리

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe inorganic solids removed by filtration
  3. customthe solvent removed under vacuum
  4. customto afford a dark colored oil
  5. customfrom which low boiling fractions are removed by distillation (bp., 79° C./0.5 mm)
  6. temperatureThe pot residue is then cooled
  7. customto afford 15.9 g of crude product, which
  8. customis recrystallized from ligroin/acetone

출처 및 근거

ORD 기록
ord-67f4c244bd2a4220b9f4d616e304c920
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04259510

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