Hydrochloric Acid → 2,2,2-Trifluoro-4'-methoxyacetophenone

HRID 1530805Notes

Reaction equation

HRID 1530805 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1.[F:11][C:12]([F:18])([F:17])[C:13](OC)=[O:14].Cl>C1COCC1.CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:13](=[O:14])[C:12]([F:18])([F:17])[F:11])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 9893Methyl trifluoroacetateHCID 178491912HCID 178491912, compound

Product 1

HCID 1365552,2,2-Trifluoro-4'-methoxyacetophenone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

At −60° C., a solution of 10.5 g of 4-methoxyphenylmagnesium bromide in 50 ml of THF was added dropwise over a period of 1 hour to a solution of 7.2 g of methyl trifluoroacetate in 50 ml of ether. Stirring was then continued at −20° C. for 2 hours and at 0° C. for a further hour. The reaction solution was mixed with 25 ml of 2N hydrochloric acid and extracted with ethyl acetate. The extract was dried and concentrated. The residue was distilled under reduced pressure (b.p. 41° C., 4.5×10−1 torr), to give the title product as a colourless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract was dried
  3. concentrationconcentrated
  4. distillationThe residue was distilled under reduced pressure (b.p. 41° C., 4.5×10−1 torr)

Sources & evidence

ORD record
ord-9897420e21a24dd2843fc9a4e3e6630b
Source dataset
uspto-grants-2001_03
Patent number
US06197729B1

Reaction notes

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