Hydrochloric Acid → 2-(4-Chloro-3-methoxyphenyl)-2-methylpropanenitrile

HRID 61799

反応式

HRID 61799 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](F)=[CH:4][C:3]=1[O:9][CH3:10].[C:11](#[N:15])[CH:12]([CH3:14])[CH3:13].C[Si]([N-][Si](C)(C)C)(C)C.[K+].Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]([CH3:14])([CH3:13])[C:11]#[N:15])=[CH:4][C:3]=1[O:9][CH3:10]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6559IsobutyronitrileHCID 27245202-Chloro-5-fluoroanisoleHCID 3251421Potassium bis(trimethylsilyl)amide

生成物 1

HCID 179891552-(4-Chloro-3-methoxyphenyl)-2-methylpropanenitrile収率 31%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
65 °C

実験手順

1-Chloro-4-fluoro-2-methoxy-benzene (4.3 g, 26.78 mmol) and isobutyronitrile (9.61 mL, 4.0 eq.) were dissolved in toluene (9.0 mL), added with KHMDS (80 mL, 0.5 M toluene solution) and stirred at 65° C. for 2 hr. The reaction solution was cooled to room temperature, added with aqueous solution of 1 N hydrochloric acid and then extracted with MTBE. The organic layer was washed with saturated brine and dried over magnesium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (1.72 g, 31%).

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionextracted with MTBE
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. customthe residues obtained
  7. concentrationafter concentration under reduced pressure
  8. customwere purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-1515b36c859648d1a5dd4503c6364978
出典データセット
uspto-grants-2016_09
特許番号
US09440922B2

関連ノート

読み込み中…