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

HRID 2274529ノート

反応式

HRID 2274529 の反応式
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]

参加物

4

反応物 2

HCID 87426929N-Methoxy-N-methyl-3-(1,1,2,2-tetrafluoroethoxy)benzamideHCID 178418573HCID 178418573、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-075c418ed7ce4f118dd98dd015e5e640
出典データセット
uspto-grants-2015_09
特許番号
US09126976B2

反応ノート

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