4-Bromopyridine-3-carbaldehyde → HCID 21600779, compound

HRID 2242111Notes

Reaction equation

HRID 2242111 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=[O:9].[C:10]1([Mg]Br)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[OH:9]

Participants

4

Reactant 2

HCID 111167404-Bromopyridine-3-carbaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 21600779HCID 21600779, 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 phenylmagnesium bromide solution in THF (1.08 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 (4-bromo-pyridin-3-yl)-phenyl-methanol 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-366fa280f9d34452855ab4783400c3f8
Source dataset
uspto-grants-2010_03
Patent number
US07671065B2

Reaction notes

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