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

HRID 66642Notes

Reaction equation

HRID 66642 reaction equation
C([O:3][C:4](=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)[CH2:5][F:6])C.Cl>C(OCC)C>[F:6][CH2:5][C:4](=[O:3])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 540772352-Ethoxy-1-fluoro-3-(3-methoxyphenyl)prop-2-ene

Product 1

HCID 205306171-Fluoro-3-(3-methoxyphenyl)-2-propanoneYield 98.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Ethoxy-1-fluoro-3-(3-methoxyphenyl)prop-2-ene (8.40 g, 0.040 mol) is stirred with a saturated solution of hydrogen chloride in diethyl ether (80 ml) overnight. The ether layer is separated, washed with water, dried (MgSO4) and filtered. Concentration of the solvent affords 1-fluoro-3-(3-methoxyphenyl)-2-propanone (7.200 g); NMR (CDCl3): 3.73 ppm (m, 5H); 4.77 ppm (d, JHF =48 Hz, 2H); 6.57-7.33 ppm (m, 4H).

Workup

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

Sources & evidence

ORD record
ord-e14898658dde410eba4a7fd2917d48e1
Source dataset
uspto-grants-1982_08
Patent number
US04342780

Reaction notes

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