4-Bromopyridine-3-carbaldehyde → HCID 10856542, compound

HRID 1712070Notes

Reaction equation

HRID 1712070 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=[O:9].[CH3:10][Mg]Br>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]([OH:9])[CH3:10]

Participants

4

Reactant 2

HCID 111167404-Bromopyridine-3-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 10856542HCID 10856542, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-bromo-pyridine-3-carbaldehyde (400 mg, 2.15 mmol) in THF (10 mL) at −78° C. was added dropwise 3.0 M methylmagnesium bromide solution in THF (1.08 mL). After 15 min, the reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate, then purified by flash chromatography eluted with 50% ethyl acetate in hexane to yield 1-(4-bromo-pyridin-3-yl)-ethanol as white crystals.

Workup

  1. customthe reaction mixture was quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. custompurified by flash chromatography
  4. washeluted with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-347a53043f3a4ade9edf3358d05d303d
Source dataset
uspto-grants-2010_09
Patent number
US07790895B2

Reaction notes

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