Water → 1-Cyclopropyl-1-(2,4-difluorophenyl)ethanol

HRID 561416

Reaction equation

HRID 561416 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[CH:12]1([Mg]Br)[CH2:14][CH2:13]1.O.C(OCC)(=O)C>C(OCC)C.O1CCCC1>[CH:12]1([C:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])([OH:11])[CH3:10])[CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 677702,4-DifluoroacetophenoneHCID 178418630HCID 178418630, compound

Product 1

HCID 247496791-Cyclopropyl-1-(2,4-difluorophenyl)ethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.50 g (9.61 mmol) of 2′,4′-difluoroacetophenone were dissolved at 0° C. in 8 ml of diethyl ether, and 38.4 ml (19.21 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran were slowly added dropwise. Stirring at 0° C. for 1 h was followed by warming to RT, and the reaction solution was mixed with water and ethyl acetate, and the phases were separated. The organic phase was washed with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the solvents were removed in vacuo. The crude product was purified by preparative HPLC (mobile phase: acetonitrile-water gradient) to result in 0.63 g (33% of theory) of the title compound.

Workup

  1. temperatureby warming to RT
  2. customthe phases were separated
  3. washThe organic phase was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customthe solvents were removed in vacuo
  6. customThe crude product was purified by preparative HPLC (mobile phase: acetonitrile-water gradient)

Sources & evidence

ORD record
ord-52d7e875ed7d481392633e4421a1c829
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Linked notes

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