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

HRID 471056ノート

反応式

HRID 471056 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-8ec6ba4d95e14b8384dd1883f83e3391
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

反応ノート

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