Hydrochloric Acid → HCID 66668931, compound

HRID 1618008Notes

Reaction equation

HRID 1618008 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[CH2:9][C:10]([C:12]2[CH:13]=[N:14][C:15]([O:18]C)=[CH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1.Cl.C(OCC)(=O)C>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15](=[O:18])[NH:14][CH:13]=2)=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 67015748HCID 67015748, compound

Product 1

HCID 66668931HCID 66668931, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-(4-bromophenyl)-3-(2,4-difluorophenyl)-1-(6-methoxypyridin-3-yl)propan-1-one (0.245 g, 567 μmol) in dioxane (6 mL) was added 37% hydrochloric acid (1.23 g, 1.04 mL, 12.5 mmol) and the resulting mixture was heated at 100° C. for 1½ h. After cooling to room temperature, the reaction mixture was poured on water and ethyl acetate and the layers were separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, filtered, and evaporated. Off-white solid (0.227 g, 95%). MS (ESI−): m/z=418.0 ([M−H]−).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. washThe organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-598efbffe59846839fb9b1a41a018105
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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