(Diethylamino)sulfur trifluoride → 1-fluoro-3-(2,4,6-trichloro-phenyl)-propan-2-one O-methyl-oxime

HRID 1039348ノート

反応式

HRID 1039348 の反応式
[CH3:1][O:2][N:3]=[C:4]([CH2:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=1[Cl:16])[CH2:5]O.C(N(S(F)(F)[F:23])CC)C>ClCCl>[CH3:1][O:2][N:3]=[C:4]([CH2:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=1[Cl:16])[CH2:5][F:23]

参加物

4

反応物 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 866790761-hydroxy-3-(2,4,6-trichloro-phenyl)-propan-2-one O-methyl-oxime

生成物 1

HCID 866790771-fluoro-3-(2,4,6-trichloro-phenyl)-propan-2-one O-methyl-oxime収率 111.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
20 °C

実験手順

To a stirred brown suspension of 1-hydroxy-3-(2,4,6-trichloro-phenyl)-propan-2-one O-methyl-oxime (33 g; 117 mmol) in dichloromethane (235 ml) at −20° C. under nitrogen was added dropwise a solution of diethylaminosulfur trifluoride (16 ml; 123 mmol) in dichloromethane (62 ml). During addition, temperature rose to −10° C. The mixture turned to a brown orange solution which was allowed to warm at 20° C. and was stirred for 2 hours. The organic solution was washed with saturated hydrogen carbonate solution (200 ml), 1N hydrochloric acid (200 ml), brine (200 ml) and dried over sodium sulfate. The solvent was removed in vacuo to afford 37 g (110% of theory) of crude 1-fluoro-3-(2,4,6-trichloro-phenyl)-propan-2-one O-methyl-oxime (isomers E/Z) as a brown oil.

後処理

  1. additionDuring addition, temperature
  2. customrose to −10° C
  3. washThe organic solution was washed with saturated hydrogen carbonate solution (200 ml), 1N hydrochloric acid (200 ml), brine (200 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-225899cc8f5143a88ceb5d113038e135
出典データセット
uspto-grants-2013_10
特許番号
US08552049B2

反応ノート

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