Methyl trifluoromethyl ketone → HCID 86603896, compound

HRID 1948773Notes

Reaction equation

HRID 1948773 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([CH3:12])[CH:10]=[CH2:11])=[C:4]([Cl:13])[C:3]=1[Cl:14].FC(F)(F)C(C)=[O:18].C(=O)(O)[O-].[Na+].OOS([O-])=O.[K+]>O.C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([CH:10]2[CH2:11][O:18]2)[CH3:12])=[C:4]([Cl:13])[C:3]=1[Cl:14]

Participants

7

Reactant 4

HCID 9871Methyl trifluoromethyl ketoneHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 68771318HCID 68771318, compound

Product 1

HCID 86603896HCID 86603896, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

1-Bromo-2,3-dichloro-4-(1-methyl-allyloxy)-benzene (2.5 g), 1,1,1-trifluoroacetone (6.05 mL) and sodium bicarbonate (2.12 g) were taken up in a solvent mixture of acetonitrile and water (2:1, 45 mL) and cooled to 0° C. Oxone (5.19 g) was added in three portions and the reaction was slowly warmed to room temperature. Upon completion the reaction was filtered and concentrated and re-dissolved in ethyl acetate. This solution was washed with saturated NH4Cl, brine and dried over sodium sulfate. Upon filtration, it was concentrated and purified by flash column chromatography eluting with EtOAc in hexanes to get the desired product (2.39 g) in 91% yield as white solid. 1H-NMR (400 MHz, CDCl3) δ: 7.48 (d, 2H), 6.97 (d, 1H), 6.83 (d, 1H), 4.40-4.38 (m, 1H), 4.15-4.08 (m, 1H), 3.25-3.21 (m, 1H), 3.18-3.16 (m, 1H), 2.89 (t, 1H), 2.85-2.68 (m, 3H), 1.49-1.44 (m, 6H).

Workup

  1. temperaturethe reaction was slowly warmed to room temperature
  2. filtrationUpon completion the reaction was filtered
  3. concentrationconcentrated
  4. dissolutionre-dissolved in ethyl acetate
  5. washThis solution was washed with saturated NH4Cl, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationUpon filtration, it
  8. concentrationwas concentrated
  9. custompurified by flash column chromatography
  10. washeluting with EtOAc in hexanes

Sources & evidence

ORD record
ord-be3a7f6e0ad043f391465516033a007e
Source dataset
uspto-grants-2013_03
Patent number
US08399517B2

Reaction notes

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