2-Bromonicotinaldehyde → 1-(2-bromopyridin-3-yl)ethanol

HRID 1716296Notes

Reaction equation

HRID 1716296 reaction equation
[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:10][Mg]Br>C1COCC1>[Br:1][C:2]1[C:7]([CH:8]([OH:9])[CH3:10])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 47149512-BromonicotinaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 104428211-(2-bromopyridin-3-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-bromo-pyridine-3-carbaldehyde (0.14 g, 0.75 mmol) in dry THF (10 mL) was dropwise added methylmagnesium bromide (1.4 M, 0.59 mL, 0.82 mmol) at −20° C. The reaction was allowed to warm to 0° C. for 20 min and then quenched with aqueous ammonium chloride solution. The usual work up gave a crude material, which was purified by chromatography (silica gel, 40% EtOAc/hexanes). 1H NMR (300 MHz, CDCl3) 8.30 (m, 1H), 7.96 (m, 1H), 7.34 (m, 1H), 5.21 (q, 1H), 1.54 (d, 3H).

Workup

  1. customat −20° C
  2. customquenched with aqueous ammonium chloride solution

Sources & evidence

ORD record
ord-5e127475af4247a8b582ec6628ba8e4b
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

Loading…