Ethanol → Ethyl 4-fluoro-3-hydroxybenzoate

HRID 645581Notes

Reaction equation

HRID 645581 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].S(Cl)(Cl)=O.C([O-])(O)=O.[Na+].[CH2:21](O)[CH3:22]>ClCCl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:21][CH3:22])=[O:7])=[CH:4][C:3]=1[OH:11]

Participants

6

Reactant 4

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 5936354-Fluoro-3-hydroxybenzoic acid

Product 1

HCID 18007712Ethyl 4-fluoro-3-hydroxybenzoateYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoro-3-hydroxy-benzoic acid (2 g, 12.81 mmol) in absolute ethanol (30 ml) was added thionyl chloride (1 ml) drop wise at 0° C. After refluxing for overnight, the solvents were driven off, the residue was dissolved in dichloromethane (50 ml), cooled on ice bath, neutralized slowly with 1M NaHCO3, and the layers were separated. The aqueous layer was extracted with dichloromethane (50 ml) for one more time. Combined organic extracts were dried (Na2SO4), filtered, concentrated, and purified by flash column chromatography using dichloromethane to yield 2.2 g (93%) of product. MS (ESI+) m/z 185 (M+H)+.

Workup

  1. temperatureAfter refluxing for overnight
  2. temperaturecooled on ice bath
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with dichloromethane (50 ml) for one more time
  5. dry with materialCombined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-1c49cd5907c24c72bec718bcbd578f2d
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Reaction notes

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