3,5-Difluorobenzaldehyde → HCID 62790817, compound

HRID 521929Notes

Reaction equation

HRID 521929 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=[O:6].[CH:11]1([Mg]Br)[CH2:13][CH2:12]1>O1CCCC1>[CH:11]1([CH:5]([C:4]2[CH:3]=[C:2]([F:1])[CH:9]=[C:8]([F:10])[CH:7]=2)[OH:6])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 5881603,5-DifluorobenzaldehydeHCID 178418630HCID 178418630, compound

Product 1

HCID 62790817HCID 62790817, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3,5-difluorobenzaldehyde (1.0 g, 7.0 mmol) was dissolved in tetrahydrofuran (10 mL) was cooled in an ice bath. cyclopropylmagnesium bromide (0.5 M in THF, 1.2 equiv., 8.4 mmol) was added slowly and the mixture was stirred at 0° C. for 60 min. The reaction was quenched with sat. ammonium chloride and extracted twice with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and concentrated to give the title compound of sufficient purity to be used directly.

Workup

  1. temperaturewas cooled in an ice bath
  2. customThe reaction was quenched with sat. ammonium chloride
  3. extractionextracted twice with EtOAc
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a069916650bc481a8db48ecc2ddfeca8
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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