Hydrochloric Acid → 2'-Fluoro-6'-methoxyacetophenone

HRID 1786823Notes

Reaction equation

HRID 1786823 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10]C)[C:3]=1C#N.C[Mg]I.[CH2:15]([O:17][CH2:18][CH3:19])C.Cl>>[F:1][C:2]1[CH:9]=[CH:8][CH:19]=[C:18]([O:17][CH3:15])[C:3]=1[C:6](=[O:10])[CH3:7]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 5231012-Fluoro-6-methoxybenzonitrileHCID 178418373HCID 178418373, compound

Product 1

HCID 27373552'-Fluoro-6'-methoxyacetophenoneYield 663.4%

Procedure

A mixture of 2-fluoro-6-methoxybenzonitrile (15.94 g, 105.5 mmol) and a solution of methyl magnesium iodide in diethyl ether (3 M, 46.0 cm3, 137 mmol) was heated to 100° C. for 18 h. Upon cooling to room temperature, aqueous hydrochloric acid (3 M, 94 cm3) was added and the mixture was heated to reflux to for 4 h. When the reaction had cooled to room temperature the organic layer was separated and the aqueous phase was extracted with ethyl acetate (100 cm3). The combined organic extracts were washed with brine (100 cm3) before being dried (Na2SO4). The solvent was removed in vacuo to afford the title compound as an oil (117.7 g, 100%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux to for 4 h
  3. temperatureWhen the reaction had cooled to room temperature the organic layer
  4. customwas separated
  5. extractionthe aqueous phase was extracted with ethyl acetate (100 cm3)
  6. washThe combined organic extracts were washed with brine (100 cm3)
  7. dry with materialbefore being dried (Na2SO4)
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8d2c5f9fb5f2469080a51514c9d2be53
Source dataset
uspto-grants-2009_03
Patent number
US07507824B2

Reaction notes

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