Methyl trifluoroacetate → 2,2,2-Trifluoro-1-(4-vinylphenyl)ethanone

HRID 1007057Notes

Reaction equation

HRID 1007057 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1)=[CH2:2].[F:11][C:12]([F:18])([F:17])[C:13](OC)=[O:14]>C1COCC1>[F:11][C:12]([F:18])([F:17])[C:13]([C:6]1[CH:7]=[CH:8][C:3]([CH:1]=[CH2:2])=[CH:4][CH:5]=1)=[O:14]

Participants

4

Reactant 2

HCID 9893Methyl trifluoroacetateHCID 178436500HCID 178436500, compound

Product 1

HCID 225064842,2,2-Trifluoro-1-(4-vinylphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The (4-vinylphenyl)magnesium bromide solution of Example 1 was cooled to −78° C. using a dry ice /acetone bath and a solution of methyl trifluoroacetate (20.00 g, 156.19 mmol) in THF (25 mL) was added dropwise over 15 min. The reaction mixture was stirred in the cooling bath for 1 h, then quenched by pouring into cold 1N H2SO4. The aqueous solution was extracted with ether and the combined extracts were washed with brine, dried (Na2SO4), and concentrated to provide 17.81 g of a pale yellow oil. This material was purified by vacuum distillation to provide 12.65 g (46%) of a colorless oil: bp 59-60° C. (1.4 mm); 1H NMR (CDCl3) δ 8.05 (d, 2ArH), 7.55 (d, 2ArH), 6.79 (dd, CH═), 5.97 (dd, ═CHH), 5.51 (dd ═CHH).

Workup

  1. customquenched
  2. additionby pouring into cold 1N H2SO4
  3. extractionThe aqueous solution was extracted with ether
  4. washthe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ef1ea5b612c84277aee5f10c28418cd1
Source dataset
uspto-grants-2004_09
Patent number
US06794109B2

Reaction notes

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