Hydrochloric Acid → 1-[2-Fluoro-4-(trifluoromethyl)phenyl]-3-methylbutanol

HRID 241373

反応式

HRID 241373 の反応式
[CH2:1]([Mg]Br)[CH:2]([CH3:4])[CH3:3].[F:7][C:8]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:9]=1[CH:10]=[O:11].[Cl-].[NH4+].Cl>C1COCC1.CCOCC>[F:7][C:8]1[CH:15]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:13]=[CH:12][C:9]=1[CH:10]([OH:11])[CH2:1][CH:2]([CH3:4])[CH3:3]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 5229292-Fluoro-4-(trifluoromethyl)benzaldehydeHCID 178418816HCID 178418816、化合物

生成物 1

HCID 668834441-[2-Fluoro-4-(trifluoromethyl)phenyl]-3-methylbutanol収率 23%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To mixed solution of 2M isobutylmagnesium bromide in THF (6.25 mL) and ether (50 mL), was added dropwise a solution of 2-fluoro-4-(trifluoromethyl)benzaldehyde (2.0 g, 10 mmol) in ether (18 mL) under N2 atmosphere. The mixture was stirred at room temperature for 45 minutes, to which was added saturated aqueous ammonium chloride solution and 1M hydrochloric acid under ice-cooling. The aqueous layer was extracted with ether. The organic layer was washed with saturated aqueous sodium bicarbonate solution, saturated brine successively. After drying over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1), to give the titled compound as a yellow oil (601 mg, yield 23%).

後処理

  1. temperaturecooling
  2. extractionThe aqueous layer was extracted with ether
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, saturated brine successively
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1)

出典と根拠

ORDレコード
ord-f19fe8998cd942088cff0df91f4902de
出典データセット
uspto-grants-2014_02
特許番号
US08648208B2

関連ノート

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