N-Methoxy-N-methyl-3-(1,1,2,2-tetrafluoroethoxy)benzamide → 1-[3-(1,1,2,2-Tetrafluoroethoxy)phenyl]ethanone

HRID 2274529노트

반응식

HRID 2274529 반응식
CON(C)[C:4](=[O:18])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]([F:17])([F:16])[CH:13]([F:15])[F:14])[CH:6]=1.[CH3:20][Mg]Br>C1COCC1>[F:17][C:12]([F:16])([O:11][C:7]1[CH:6]=[C:5]([C:4](=[O:18])[CH3:20])[CH:10]=[CH:9][CH:8]=1)[CH:13]([F:14])[F:15]

참가 물질

4

반응물 2

HCID 87426929N-Methoxy-N-methyl-3-(1,1,2,2-tetrafluoroethoxy)benzamideHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 716505571-[3-(1,1,2,2-Tetrafluoroethoxy)phenyl]ethanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

N-methoxy-N-methyl-3-(1,1,2,2-tetrafluoroethoxy)benzamide (7.5 g, 25.2 mmol) was dissolved in THF (84 mL) and cooled to −78° C. Methyl magnesium bromide (3N in diethyl ether, 21.03 mL, 63.1 mmol) was added dropwise and the resulting reaction mixture was stirred for 30 min. The reaction was warmed to 25° C. over 30 minutes and then was quenched by addition to an Erlenmeyer flask containing ice and saturated ammonium chloride solution. This mixture was extracted with EtOAc, the organic layers were collected and dried with anhydrous magnesium sulfate, then filtered and concentrated. Crude material obtained corresponds to 1-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]ethanone. 1H NMR (400 MHz, CDCl3) δ 2.62 (s, 3H), 5.96 (t, t, J=53, 2.7 Hz, 1H), 7.43 (d, J=8.1 Hz, 1H), 7.51 (t, J=8.0 Hz, 1H), 7.80 (s, 1H), 7.88 (d, J=7.8 Hz, 1H).

후처리

  1. customthe resulting reaction mixture
  2. temperatureThe reaction was warmed to 25° C. over 30 minutes
  3. customwas quenched by addition to an Erlenmeyer flask
  4. additioncontaining ice and saturated ammonium chloride solution
  5. extractionThis mixture was extracted with EtOAc
  6. customthe organic layers were collected
  7. dry with materialdried with anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-075c418ed7ce4f118dd98dd015e5e640
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126976B2

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