Water → HCID 58392238, compound

HRID 561475Notes

Reaction equation

HRID 561475 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=1.C(OCC)C.[CH:16]1([Mg]Br)[CH2:18][CH2:17]1.O>C1COCC1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([CH:16]2[CH2:18][CH2:17]2)[OH:7])=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 27249084-Chloro-2-fluorobenzaldehydeHCID 178418630HCID 178418630, compound

Product 1

HCID 58392238HCID 58392238, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.00 g (6.31 mmol) of 4-chloro-2-fluorobenzaldehyde were introduced into 20 ml of diethyl ether at 0° C., 19 ml (9.46 mmol) of 0.5N cyclopropylmagnesium bromide solution in THF were added, and the mixture was stirred at RT overnight. The reaction mixture was added to water, the phases were separated, the aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water) to result in 730 mg (58% of theory) of the title compound.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialthe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water)

Sources & evidence

ORD record
ord-6eb7c04746cf4d7d92e7076481af17a7
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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