Trifluoroacetic acid → (4-tert-Butyl-3,5-difluorophenoxy)acetic acid

HRID 2108830

반응식

HRID 2108830 반응식
C([O:5][C:6](=[O:21])[CH2:7][O:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([C:16]([CH3:19])([CH3:18])[CH3:17])=[C:11]([F:20])[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:16]([C:12]1[C:11]([F:20])=[CH:10][C:9]([O:8][CH2:7][C:6]([OH:21])=[O:5])=[CH:14][C:13]=1[F:15])([CH3:19])([CH3:17])[CH3:18]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 90843131Tert-butyl(4-tert-butyl-3,5-difluorophenoxy)acetate

생성물 1

HCID 68804332(4-tert-Butyl-3,5-difluorophenoxy)acetic acid수율 77.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of sodium hydride (75 mg, 1.9 mmol) in THF (5 ml) was added 4-tert-butyl-3,5-difluorophenol (290 mg, 1.6 mmol) at 0° C., followed by stirring for 30 minutes. Then, tert-butyl bromoacetate (370 mg, 1.9 mmol) was added and the mixture was refluxed at 90° C. for 1 hour. The reaction was quenched with saturated ammonium chloride aqueous solution and the product was extracted with EtOAc, washed with brine, dried over magnesium sulfate. Then, filtration, evaporation, and purification through silica gel column chromatography eluting with hexane/EtOAc (20:1 to 4:1) gave the tert-butyl(4-tert-butyl-3,5-difluorophenoxy)acetate (403 mg, 86%). The DCM (2.0 ml) solution of tert-butyl(4-tert-butyl-3,5-difluorophenoxy)acetate (400 mg, 1.34 mmol) and TFA (2.0 ml), was stirred for 1 hour at room temperature. Evaporation gave the residue which was triturated with Hexane to furnish the title compound as a white solid (253 mg, 77%). 1H NMR (300 MHz, CDCl3): δ 1.42 (9H, t, J=2.2 Hz), 4.63 (2H, s), 6.39 (2H, d, J=12.1 Hz). MS (ESI) m/z 243 (M−H)−.

후처리

  1. customEvaporation
  2. customgave the residue which
  3. customwas triturated with Hexane

출처 및 근거

ORD 기록
ord-4904f02467ca4b218176eaef9d593c9f
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514457B2

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