Pyridine → 1-(4-Bromo-3-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-one

HRID 1848313ノート

反応式

HRID 1848313 の反応式
S(Cl)(Cl)=O.N1C=CC=CC=1.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:34])[CH2:19][C:20]([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=2)(O)[C:21]([F:24])([F:23])[F:22])=[CH:14][C:13]=1[CH3:35]>C1(C)C=CC=CC=1>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:34])[CH:19]=[C:20]([C:26]2[CH:27]=[C:28]([Cl:33])[CH:29]=[C:30]([Cl:32])[CH:31]=2)[C:21]([F:23])([F:24])[F:22])=[CH:14][C:13]=1[CH3:35]

参加物

5

反応物 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 866264261-(4-Bromo-3-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutan-1-one

生成物 1

HCID 765635821-(4-Bromo-3-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-one収率 84.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

0.391 g of thionyl chloride and 0.104 g of pyridine were added to toluene (3 g) solution of 0.3 g of 1-(4-bromo-3-methylphenyl)-3-(3,5-dichlorophenyl)-3-hydroxy-4,4,4-trifluorobutan-1-one synthesized in Step 3 at room temperature and stirred for 1 hour at 80° C. After completion of the reaction, the reaction solution was cooled to room temperature, and separated by adding toluene and 2N hydrochloric acid. The organic phase was washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Although the obtained residue includes a mixture of geometric isomers, this residue was purified by silica gel column chromatography which eluted the residue with ethyl acetate-hexane (1:10) to obtain 0.244 g of the target product as a yellow solid.

後処理

  1. customAfter completion of the reaction
  2. temperaturethe reaction solution was cooled to room temperature
  3. customseparated
  4. additionby adding toluene and 2N hydrochloric acid
  5. washThe organic phase was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. additiona mixture of geometric isomers
  9. customthis residue was purified by silica gel column chromatography which
  10. washeluted the residue with ethyl acetate-hexane (1:10)

出典と根拠

ORDレコード
ord-2128fb8fe784435d80df0afa7c92bea3
出典データセット
uspto-grants-2015_02
特許番号
US08952175B2

反応ノート

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