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

HRID 471056노트

반응식

HRID 471056 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8ec6ba4d95e14b8384dd1883f83e3391
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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