3-Chloro-2-fluoro-6-(trifluoromethyl)benzaldehyde → HCID 86721087, compound

HRID 1396309Notes

Reaction equation

HRID 1396309 reaction equation
[Cl:1][C:2]1[C:3]([F:14])=[C:4]([C:7]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH:15]([Mg]Br)=[CH2:16]>C1COCC1>[Cl:1][C:2]1[C:3]([F:14])=[C:4]([CH:5]([OH:6])[CH:15]=[CH2:16])[C:7]([C:10]([F:12])([F:13])[F:11])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 7363373-Chloro-2-fluoro-6-(trifluoromethyl)benzaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 86721087HCID 86721087, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-chloro-2-fluoro-6-(trifluoromethyl)benzaldehyde (2.052 g, 9.06 mmol) in THF (30 mL) under nitrogen at −78° C. was added dropwise vinyl magnesium bromide (1 M in THF) (11.77 mL, 11.77 mmol). The mixture was stirred for 15 minutes at this temperature then the cooling bath was removed allowing the solution to warm to ambient temperature where it was stirred for 1 h. The reaction was cooled to 0° C. and quenched with 20 mL of aqueous NH4Cl (saturated) and the solvent was removed under a stream of nitrogen. The solid residue was taken up in water/ethyl acetate and phases were separated. The aqueous layer was extracted twice with ethyl acetate and the combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated to give an oil. The oil was then purified using silica gel chromatography. The desired fractions were combined together to give 1-(3-chloro-2-fluoro-6-(trifluoromethyl)phenyl)prop-2-en-1-ol (1.322 g, 57%) as a faint yellow colored oil.

Workup

  1. customthe cooling bath was removed
  2. stirringwas stirred for 1 h
  3. temperatureThe reaction was cooled to 0° C.
  4. customquenched with 20 mL of aqueous NH4Cl (saturated)
  5. customthe solvent was removed under a stream of nitrogen
  6. customphases were separated
  7. extractionThe aqueous layer was extracted twice with ethyl acetate
  8. washthe combined organic extracts were washed with brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto give an oil
  13. customThe oil was then purified

Sources & evidence

ORD record
ord-1c7d4d27a8d94bd5a2b6cef63beb141c
Source dataset
uspto-grants-2014_12
Patent number
US08901115B2

Reaction notes

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