Chloride → HCID 18009122, compound

HRID 987493Notes

Reaction equation

HRID 987493 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[F:10].[Cl-].[CH2:12]1[CH2:16]OC[CH2:13]1>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH2:16][CH:12]=[CH2:13])=[CH:4][C:3]=1[F:10]

Participants

4

Reactant 3

HCID 312Chloride2×HCID 8028Tetrahydrofuran2×HCID 27834114-Bromo-3-fluorobenzaldehyde

Product 1

HCID 18009122HCID 18009122, compound

Procedure

To a solution of the aldehyde from Step F (7.97 g, 39.1 mmol) in 40 mL of THF at −78° C. under argon was added dropwise a solution of allymagnesium chloride in THF (23.4 mL, 46.9 mmol, 2M). After one hour, another portion of allymagnesium chloride solution was added (5 mL, 10 mmol). After an additional 30 minutes, the solution was quenched with saturated aqueous ammonium chloride, warmed to room temperature, and poured into ethyl acetate. The solution was washed with washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product.

Workup

  1. waitAfter an additional 30 minutes
  2. customthe solution was quenched with saturated aqueous ammonium chloride
  3. additionpoured into ethyl acetate
  4. washThe solution was washed
  5. washwith washed with sat. aq. NaHCO3 and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00e61a1dddb44e96ba5c8cab20ebffb0
Source dataset
uspto-grants-2003_10
Patent number
US06632818B2

Reaction notes

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