Aluminium lithium hydride → 2-(3-Bromophenyl)-2-fluoroethanol

HRID 1689287ノート

反応式

HRID 1689287 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[C:10]([CH:14]([F:20])[C:15](OCC)=[O:16])[CH:11]=[CH:12][CH:13]=1>C1COCC1>[Br:7][C:8]1[CH:9]=[C:10]([CH:14]([F:20])[CH2:15][OH:16])[CH:11]=[CH:12][CH:13]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 57989125Ethyl 2-(3-bromophenyl)-2-fluoroacetate

生成物 1

HCID 579893062-(3-Bromophenyl)-2-fluoroethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium aluminum hydride (1M in THF, 13.0 mL) was added portionwise over 7 minutes to a solution of ethyl 2-(3-bromophenyl)-2-fluoroacetate (example 39, step a) (2.94 g) in THF (35 mL), pre-cooled in ice-water. The resulting mixture was stirred in ice-water for 30 minutes, then quenched by the careful addition of methanol (5 mL), added portionwise over 30 minutes. The mixture was poured into 2 molar aqueous HCl and extracted three times with ethyl, acetate. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulphate and purified by flash chromatography on silica eluted with 25% diethyl ether in isohexane to afford the subtitled compound as colourless oil. Yield 1.39 g.

後処理

  1. customquenched by the careful addition of methanol (5 mL)
  2. additionadded portionwise over 30 minutes
  3. additionThe mixture was poured into 2 molar aqueous HCl
  4. extractionextracted three times with ethyl, acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over anhydrous magnesium sulphate
  7. custompurified by flash chromatography on silica
  8. washeluted with 25% diethyl ether in isohexane

出典と根拠

ORDレコード
ord-ffd6f84d6b534f17b8b8ce25f3585c4d
出典データセット
uspto-grants-2012_04
特許番号
US08148373B2

反応ノート

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