Carbon tetrabromide → 4-(Bromomethyl)-2-methoxypyridine

HRID 1972668Notes

Reaction equation

HRID 1972668 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9]O)[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:7]1[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 14462410(2-Methoxypyridin-4-yl)methanol

Product 1

HCID 198054314-(Bromomethyl)-2-methoxypyridineYield 89.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 100-mL round-bottomed flask was added (2-methoxy-4-pyridinyl)methanol (1.52 g, 10.92 mmol), triphenylphosphine (3.15 g, 12.02 mmol, Aldrich, St. Louis, Mo.), and carbon tetrabromide (1.165 mL, 12.02 mmol, Aldrich, St. Louis, Mo.) in DCM (20 mL). The reaction mixture was stirred at 0° C. for 2 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 20% EtOAc/hexanes to give 4-(bromomethyl)-2-methoxypyridine (1.98 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-b0103361177645e7b7c8047be594a141
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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