5-Chloro-2-(difluoromethoxy)benzaldehyd → HCID 86721086, compound

HRID 1396308Notes

Reaction equation

HRID 1396308 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]([F:13])[F:12])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH:14]([Mg]Br)=[CH2:15]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]([F:12])[F:13])=[C:6]([CH:7]([OH:8])[CH:14]=[CH2:15])[CH:9]=1

Participants

4

Reactant 2

HCID 47709495-Chloro-2-(difluoromethoxy)benzaldehydHCID 178418507HCID 178418507, compound

Product 1

HCID 86721086HCID 86721086, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

5-Chloro-2-(difluoromethoxy)benzaldehyde (0.480 g, 2.324 mmol) was dissolved in dry THF (11.62 mL) and the reaction was cooled to −78° C. under argon. Vinyl magnesium bromide (3.49 mL, 3.49 mmol) was then added dropwise. After the reaction was complete, the ice bath was removed and reaction was allowed to warm to rt and stirred for an additional 2 h. The reaction was cooled to 0° C. and then carefully quenched with saturated ammonium chloride. The mixture was then diluted with water and extracted with EtOAc (3×). The combined organic phases were dried over Na2SO4, filtered and concentrated to yield 1-(5-chloro-2-(difluoromethoxy)phenyl)prop-2-en-1-ol (561 mg, 103%) as a clear oil. MS (ESI) m/z: 236.9 (M+H, Chlorine isotope peak)+.

Workup

  1. customthe ice bath was removed
  2. customreaction
  3. temperatureto warm to rt
  4. temperatureThe reaction was cooled to 0° C.
  5. customcarefully quenched with saturated ammonium chloride
  6. additionThe mixture was then diluted with water
  7. extractionextracted with EtOAc (3×)
  8. dry with materialThe combined organic phases were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-3ad229c87ba9493ca16a142808fb960a
Source dataset
uspto-grants-2014_12
Patent number
US08901115B2

Reaction notes

Loading…