Water → HCID 11052309, compound

HRID 1530801Notes

Reaction equation

HRID 1530801 reaction equation
CN(P(N(C)C)N(C)C)C.Br[C:12](Br)([F:14])[F:13].[CH3:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)=O.O>COCCOCCOCCOC>[F:13][C:12]([F:14])=[C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6382DibromodifluoromethaneHCID 74764'-MethoxyacetophenoneHCID 15355Hexamethylphosphorous triamide

Product 1

HCID 11052309HCID 11052309, compound

Reagents, catalysts & solvents 1

HCID 8189TriglymeSolvent3×

Conditions

Temperature
80 °C

Procedure

At between 0° C. and −10° C., 181 g of tris(dimethylamino)phosphine in 75 ml of triglyme were added dropwise to 84 g of dibromodifluoromethane in 50 ml of triglyme. At 0° C., 30 g of 4-methoxyacetophenone dissolved in 125 ml of triglyme were subsequently added dropwise and the mixture was stirred for ½ h at room temperature and for 24 h at 80° C. The mixture was cooled to room temperature, mixed with 200 ml of water and extracted with petroleum ether. The combined organic phases were dried and concentrated. For purification, the crude product was chromatographed over silica gel (petroleum ether/ethyl acetate 5:1), to give the title product as a colourless oil.

Workup

  1. additionwere subsequently added dropwise
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with petroleum ether
  4. customThe combined organic phases were dried
  5. concentrationconcentrated
  6. customFor purification
  7. customthe crude product was chromatographed over silica gel (petroleum ether/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-76d3658e32bc47d59494f76baa9aae57
Source dataset
uspto-grants-2001_03
Patent number
US06197729B1

Reaction notes

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