4-Bromopyridine-3-carbaldehyde → 1-(4-Bromo-pyridin-3-yl)-2-methyl-propan-1-ol

HRID 1712072Notes

Reaction equation

HRID 1712072 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=[O:9].[CH:10]([Mg]Br)([CH3:12])[CH3:11]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]([OH:9])[CH:10]([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 111167404-Bromopyridine-3-carbaldehydeHCID 178418365HCID 178418365, compound

Product 1

HCID 592051921-(4-Bromo-pyridin-3-yl)-2-methyl-propan-1-ol

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 1.0 M isopropyl-magnesium bromide solution in THF (3.23 mL). After 15 min, the reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate, then purification by flash chromatography eluted with 50% ethyl acetate in hexane to yield 1-(4-bromo-pyridin-3-yl)-2-methyl-propan-1-ol as slight yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-db9281c220384cdb9385a95dea3da23b
Source dataset
uspto-grants-2010_09
Patent number
US07790895B2

Reaction notes

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