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

HRID 2242110Notes

Reaction equation

HRID 2242110 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. customAfter 15 min. the 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-51c784229cdd42108a8dd30a156e8a80
Source dataset
uspto-grants-2010_03
Patent number
US07671065B2

Reaction notes

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