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

HRID 1689287Notes

Reaction equation

HRID 1689287 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ffd6f84d6b534f17b8b8ce25f3585c4d
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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