3-Fluorosalicylaldehyde → 2-Fluoro-6-(1-hydroxyethyl)phenol

HRID 858640Notes

Reaction equation

HRID 858640 reaction equation
[CH3:1][Li].[F:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[OH:12]>C1COCC1>[F:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:6]([CH:7]([OH:8])[CH3:1])[C:5]=1[OH:12]

Participants

4

Reactant 2

HCID 5877883-FluorosalicylaldehydeHCID 178418348HCID 178418348, compound

Product 1

HCID 450831602-Fluoro-6-(1-hydroxyethyl)phenolYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl lithium (25.5 mL, 35.7 mmol, 1.4M in ether) was added to a cooled −78° C. solution of 3-fluorosalicylaldehyde (2 g, 14.3 mmol) dissolved in THF (50 mL). The reaction mixture was stirred for 3 hours and then warmed up to room temperature. After 3 hours the reaction was quenched with saturated NH4Cl and extracted with EtOAc. The organic extracts were washed with 1N HCl, brine, dried over Na2SO4 and concentrated to an oil. The oil was purified by flash column chromatography (0% to 20% EtOAc in hexanes) to give the title compound as a clear oil (2.2 g, 99%). 1H NMR (400 MHz, CDCl3): δ 1.58 (d, J=6.6 Hz, 3 H), 2.68 (s, 1 H), 5.13 (m, 1 H), 6.78 (td, J=7.8, 4.8 Hz, 1 H), 6.87 (d, J=7.6, 1 H), 6.99 (m, 1 H), 7.33 (s, 1 H).

Workup

  1. customAfter 3 hours the reaction was quenched with saturated NH4Cl
  2. extractionextracted with EtOAc
  3. washThe organic extracts were washed with 1N HCl, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to an oil
  6. customThe oil was purified by flash column chromatography (0% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-010dd6fa2e5e4630a10d7fb670bb9aa9
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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