Ethanol → Benzoic acid, 2-fluoro-5-(trifluoromethyl)-, ethyl ester

HRID 76303노트

반응식

HRID 76303 반응식
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].CCN(CC)CC.[CH3:22][CH2:23][OH:24]>C1COCC1>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([O:24][CH2:23][CH3:22])=[O:5]

참가 물질

5

반응물 3

HCID 702EthanolHCID 8471TriethylamineHCID 27348802-Fluoro-5-(trifluoromethyl)benzoyl Chloride

생성물 1

HCID 46311387Benzoic acid, 2-fluoro-5-(trifluoromethyl)-, ethyl ester수율 92.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-fluoro-5-(trifluoromethyl)benzoyl chloride (5.0 g, 22.0 mmol) in THF (25 mL) was added Et3N (3.1 mL, 22.0 mmol) followed by EtOH (1.3 mL, 22.0 mmol). This mixture was stirred at ambient temperature for 1 h and quenched with saturated, aqueous NH4Cl (10 mL). The layers were separated and the aqueous layer was extracted with 3×10 mL EtOAc and the combined organics were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (SiO2, 60% hexanes in EtOAc) to give the title compound (4.8 g, 20.3 mmol, 92% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.42 (t, J=7.1 Hz, 3 H), 4.43 (q, J=7.1 Hz, 2 H), 7.23-7.34 (m, 1 H), 7.74-7.82 (m, 1 H), 8.23 (dd, J=6.3, 2.4 Hz, 1 H).

후처리

  1. customquenched with saturated, aqueous NH4Cl (10 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with 3×10 mL EtOAc
  4. dry with materialthe combined organics were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by column chromatography (SiO2, 60% hexanes in EtOAc)

출처 및 근거

ORD 기록
ord-6ad123aa98ca491fb1847e6548bd8c08
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835475B2

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