Hydrochloric Acid → 1-Fluoro-3-(4-methoxyphenyl)-2-propanone

HRID 66640Notes

Reaction equation

HRID 66640 reaction equation
C([O:3][C:4](=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[CH2:5][F:6])C.Cl.O>C(OCC)C>[F:6][CH2:5][C:4](=[O:3])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 54557256HCID 54557256, compound

Product 1

HCID 152671761-Fluoro-3-(4-methoxyphenyl)-2-propanoneYield 96.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Ethoxy-1-fluoro-3-(4-methoxyphenyl)prop-2-ene (5 g, 0.024 mol) is stirred with a saturated solution of hydrogen chloride in diethyl ether (40 ml) overnight. Water (18 ml) is added and the stirring is continued for another 3 hours. The ether layer is separated, washed with water, dried (MgSO4), and filtered. Concentration of the solvent affords 1-fluoro-3-(4-methoxyphenyl)-2-propanone (4.2 g); NMR (CDCl3): 6.7-7.3 ppm (4H, m), 4.8 ppm (2H, J=48 Hz), 3.7-3.9 ppm (5H, m).

Workup

  1. customThe ether layer is separated
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-908a33d1b9474d65860bc5e24171fa44
Source dataset
uspto-grants-1982_08
Patent number
US04342780

Reaction notes

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