Carbon tetrabromide → 3-(Bromomethyl)-2-methoxypyridine

HRID 1972651Notes

Reaction equation

HRID 1972651 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9]O)=[CH:7][CH:6]=[CH:5][N:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:31]>C(Cl)Cl>[Br:31][CH2:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 10630565(2-Methoxypyridin-3-yl)methanol

Product 1

HCID 575745123-(Bromomethyl)-2-methoxypyridineYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100-mL round-bottomed flask was added (2-methoxy-3-pyridinyl)methanol (1.12 g, 8.05 mmol), triphenylphosphine (2.32 g, 8.85 mmol, Aldrich, St. Louis, Mo.) and carbon tetrabromide (0.86 mL, 8.85 mmol, Aldrich, St. Louis, Mo.) in DCM (20 mL). The reaction mixture was stirred at room temperature for 3 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 20% EtOAc/hexanes to give 3-(bromomethyl)-2-methoxypyridine (1.10 g) as a colorless oil.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-a5944d691ad04f7299c933935d6813ce
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

Loading…