2-Bromonicotinaldehyde → 1-(2-Bromo-pyridin-3-yl)-4-phenyl-butan-1-ol

HRID 919053Notes

Reaction equation

HRID 919053 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]=1

Participants

4

Reactant 2

HCID 47149512-BromonicotinaldehydeHCID 178418471HCID 178418471, compound

Product 1

HCID 866970881-(2-Bromo-pyridin-3-yl)-4-phenyl-butan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. waitat room temperature for 30 minutes
  2. customcomplete was quenched with 10 mL of NH4Cl (sat'd, aq.)
  3. customThe crude material was purified on silica gel (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1c0a5ec6736c4bba97a1ba8ffb48b2a3
Source dataset
uspto-grants-2016_03
Patent number
US09272990B2

Reaction notes

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