5-Chloro-2-(difluoromethoxy)benzaldehyd → HCID 86721086, 화합물

HRID 1396308노트

반응식

HRID 1396308 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]([F:13])[F:12])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH:14]([Mg]Br)=[CH2:15]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]([F:12])[F:13])=[C:6]([CH:7]([OH:8])[CH:14]=[CH2:15])[CH:9]=1

참가 물질

4

반응물 2

HCID 47709495-Chloro-2-(difluoromethoxy)benzaldehydHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 86721086HCID 86721086, 화합물수율 103%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

5-Chloro-2-(difluoromethoxy)benzaldehyde (0.480 g, 2.324 mmol) was dissolved in dry THF (11.62 mL) and the reaction was cooled to −78° C. under argon. Vinyl magnesium bromide (3.49 mL, 3.49 mmol) was then added dropwise. After the reaction was complete, the ice bath was removed and reaction was allowed to warm to rt and stirred for an additional 2 h. The reaction was cooled to 0° C. and then carefully quenched with saturated ammonium chloride. The mixture was then diluted with water and extracted with EtOAc (3×). The combined organic phases were dried over Na2SO4, filtered and concentrated to yield 1-(5-chloro-2-(difluoromethoxy)phenyl)prop-2-en-1-ol (561 mg, 103%) as a clear oil. MS (ESI) m/z: 236.9 (M+H, Chlorine isotope peak)+.

후처리

  1. customthe ice bath was removed
  2. customreaction
  3. temperatureto warm to rt
  4. temperatureThe reaction was cooled to 0° C.
  5. customcarefully quenched with saturated ammonium chloride
  6. additionThe mixture was then diluted with water
  7. extractionextracted with EtOAc (3×)
  8. dry with materialThe combined organic phases were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3ad229c87ba9493ca16a142808fb960a
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901115B2

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