Hydrochloric Acid → 1-(3,5-Difluoro-4-methoxyphenyl)-2,2,2-trifluoroethanone

HRID 587772

반응식

HRID 587772 반응식
Br[C:2]1[CH:3]=[C:4]([F:11])[C:5]([O:9][CH3:10])=[C:6]([F:8])[CH:7]=1.[F:12][C:13]([F:19])([F:18])[C:14](OC)=[O:15].Cl>C1COCC1>[F:8][C:6]1[CH:7]=[C:2]([C:14](=[O:15])[C:13]([F:19])([F:18])[F:12])[CH:3]=[C:4]([F:11])[C:5]=1[O:9][CH3:10]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 9893Methyl trifluoroacetateHCID 27732874-Bromo-2,6-difluoroanisole

생성물 1

HCID 867225781-(3,5-Difluoro-4-methoxyphenyl)-2,2,2-trifluoroethanone수율 100.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Isopropyl magnesium chloride lithium chloride complex (22.0 mL, 28.02 mmol) was added dropwise to a stirred solution of 5-bromo-1,3-difluoro-2-methoxybenzene (5.0 g, 22.42 mmol) at −5° C. in THF (100 mL) and the reaction mixture was stirred at same temperature for 30 min. Methyl trifluoroacetate (3.67 g, 28.69 mmol) was added dropwise and the reaction mixture was stirred at ambient temperature for 2 h. A 2 N HCl solution (200 mL) was added to quench the reaction and then it was extracted with diethylether. The combined organic layers were washed with brine, dried (Na2SO4) filtered and concentrated to afford the title compound (5.4 g, crude) as a yellow liquid. The material was taken to next step without further purification. 1H NMR (400 MHz, CDCl3) δ 7.68-7.60 (m, 2H) 4.19 (s, 3H); ESIMS m/z 240.1 ([M]+).

후처리

  1. stirringthe reaction mixture was stirred at ambient temperature for 2 h
  2. customto quench
  3. customthe reaction
  4. extractionit was extracted with diethylether
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c941b14a50a14027819f3d5381de4a3c
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226501B2

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