Phosphorus oxychloride → HCID 86648182, compound

HRID 1036049Notes

Reaction equation

HRID 1036049 reaction equation
O=P(Cl)(Cl)Cl.C[N+](C)=[CH:8][Cl:9].[Cl-].[F:12][CH2:13][C:14]1([CH2:21][F:22])[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]1.C([O-])(O)=O.[Na+]>ClCCl.CN(C)C=O>[Cl:9][C:8]1[CH2:18][CH2:19][C:14]([CH2:21][F:22])([CH2:13][F:12])[CH2:15][C:16]=1[CH:17]=[O:20]

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 516892Sodium BicarbonateHCID 67126736HCID 67126736, compound

Product 1

HCID 86648182HCID 86648182, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 100 mL pear flask was added N,N-dimethylformamide (498 μA) and dichloromethane (8.9 mL) to give a colorless solution. The solution was cooled to 0° C. and POCl3 (550 μA) was added dropwise and then the mixture was warmed to room temperature for 30 minutes. In the meantime, to a 100 mL pear shaped flask was added EXAMPLE 353C (870 mg, 5.36 mmol) in dichloromethane (8941 μl) to give a colorless solution. The Vilsmeier reagent was then taken up in a syringe and added dropwise to the 4,4-bis(fluoromethyl)cyclohexanone (870 mg) solution at room temperature. The resulting solution was stirred overnight. The reaction was poured into saturated aqueous NaHCO3 and ice, warmed to room temperature and extracted with dichloromethane (3×30 mL). The organics were combined, dried over MgSO4, filtered and concentrated by rotary evaporation. The residue was purified by regular phase flash column chromatography (Analogix (0-60% hexanes/ethyl acetate).

Workup

  1. customto give a colorless solution
  2. temperaturethe mixture was warmed to room temperature for 30 minutes
  3. customto give a colorless solution
  4. temperaturewarmed to room temperature
  5. extractionextracted with dichloromethane (3×30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customThe residue was purified by regular phase flash column chromatography (Analogix (0-60% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-e34b431e2a17450fb6a99fa1d8a26e84
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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