Diethyl Ether → HCID 117667393, compound

HRID 712746Notes

Reaction equation

HRID 712746 reaction equation
[Br:1][C:2]1[C:3]([Cl:10])=[C:4]([CH:8]=[O:9])[CH:5]=[N:6][CH:7]=1.[CH3:11][Mg]Br.CCOCC>C1COCC1>[Br:1][C:2]1[C:3]([Cl:10])=[C:4]([CH:8]([OH:9])[CH3:11])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 717423075-Bromo-4-chloropyridine-3-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 117667393HCID 117667393, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a round bottom flask is added 5-bromo-4-chloro-pyridine-3-carbaldehyde (490 mg, 2.22 mmol) in 10 ml of THF at 0° C., followed by the addition of methylmagnesium bromide, 3M in ether (0.89 ml, 2.67 mmol). The reaction mixture is stirred at room temperature for 1 hour. The reaction mixture is concentrated. The residue is diluted with EtOAc/saturated NH4Cl. The organic layer is separated, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude product. Purification by the flash column chromatography affords 287 mg of 1-(5-bromo-4-chloro-pyridin-3-yl)-ethanol.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additionThe residue is diluted with EtOAc/saturated NH4Cl
  3. customThe organic layer is separated
  4. washwashed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product
  9. customPurification by the flash column chromatography

Sources & evidence

ORD record
ord-a2cedaa802b24bb2ab410ed62340e52b
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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