Dimethylformamide → HCID 19086784, compound

HRID 1464601Notes

Reaction equation

HRID 1464601 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=[O:4].[CH3:12][Si:13]([CH2:16][Mg]Cl)([CH3:15])[CH3:14].CN(C)C=O.CCCCCC>C(OCC)C.O>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2([CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH2:2][O:4]2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 1202482-Chloro-4'-fluoroacetophenoneHCID 178418680HCID 178418680, compound

Product 1

HCID 19086784HCID 19086784, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

1.068 g (6.2 mmole) of 2-chloro-4'-fluoroacetophenone were dissolved in 20 ml of diethyl ether, and the ethereal solution was stirred under a stream of nitrogen, whilst 7.5 ml of an ethereal solution containing 7.4 mmole of trimethylsilylmethylmagnesium chloride was added dropwise at such a rate that the temperature of the reaction mixture did not exceed -10° C. to -5° C. The reaction mixture was then stirred for a further 15 minutes whilst being kept within this temperature range. At the end of this time, 3.5 ml of dimethylformamide were added dropwise to the reaction solution at such a rate that the temperature of the reaction mixture did not exceed -10° C. to -5° C. The reaction mixture was then stirred for a further 10 minutes and, whilst it was being kept within this temperature range, 6 ml of hexane and then 6 ml of water were added. The reaction mixture was then stirred for 5 minutes, after which it was poured into 10 ml of water and extracted with 100 ml of hexane. The organic extract was washed with 50 ml of a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, to give 1.39 g (yield 100%) of the title compound, as an oily substance.

Workup

  1. additionwas added dropwise at such a rate that the temperature of the reaction mixture
  2. customdid not exceed -10° C. to -5° C
  3. customdid not exceed -10° C. to -5° C
  4. stirringThe reaction mixture was then stirred for a further 10 minutes and, whilst it
  5. stirringThe reaction mixture was then stirred for 5 minutes
  6. extractionextracted with 100 ml of hexane
  7. extractionThe organic extract
  8. washwas washed with 50 ml of a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-57ccc11d89924d179173df2c32d75850
Source dataset
uspto-grants-1994_04
Patent number
US05306712

Reaction notes

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