Potassium Fluoride → Methyl 3-(2,5-difluoro-3-hydroxyphenyl)pentanoate

HRID 1662566Notes

Reaction equation

HRID 1662566 reaction equation
[Si]([O:8][C:9]1[C:10]([F:24])=[C:11]([CH:16]([CH2:22][CH3:23])[CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:12]=[C:13]([F:15])[CH:14]=1)(C(C)(C)C)(C)C.[F-].[K+]>CN(C=O)C>[F:24][C:10]1[C:9]([OH:8])=[CH:14][C:13]([F:15])=[CH:12][C:11]=1[CH:16]([CH2:22][CH3:23])[CH2:17][C:18]([O:20][CH3:21])=[O:19]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 57706858Methyl 3-(3-(tert-butyldimethylsilyloxy)-2,5-difluorophenyl)pentanoate

Product 1

HCID 57705760Methyl 3-(2,5-difluoro-3-hydroxyphenyl)pentanoateYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A screw-cap vial was charged with 90.F (0.23 g, 0.64 mmol), DMF (2.5 mL), and potassium fluoride (0.075 g, 1.3 mmol). The mixture was stirred for 5 minutes at room temperature, quenched with 1 N HCl, and diluted with EtOAc. The organics were washed with water and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford 90.G (0.13 g, 83% yield) as a colorless oil.

Workup

  1. customquenched with 1 N HCl
  2. additiondiluted with EtOAc
  3. washThe organics were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-2b29b95de0d348679f37668faff9a9cb
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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