2-Bromonicotinaldehyde → 1-(2-Bromo-pyridin-3-yl)-4-phenyl-butan-1-ol
Reaction equation
[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:10]1([CH2:16][CH2:17][CH2:18][Mg]Br)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[Br:1][C:2]1[C:7]([CH:8]([OH:9])[CH2:18][CH2:17][CH2:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-Bromo-pyridine-3-carbaldehyde (1.25 g, 6.72 mmol) was dissolved in THF (10 mL) and cooled to 0° C. 3-phenyl-propyl magnesium bromide (0.5 M in THF, 20.2 mL, 10.08 mmol) was slowly added and the reaction stirred at 0° C. for 1 hour and then at room temperature for 30 minutes. The reaction was monitored by TLC and when complete was quenched with 10 mL of NH4Cl (sat'd, aq.). The volume of THF was reduced and the reaction was submitted to EtOAc/H2O workup. The crude material was purified on silica gel (0-100% EtOAc in hexanes) to give the title compound.