Carbon tetrabromide → 3-(Bromomethyl)-2-methoxy-6-methylpyridine

HRID 79274Notes

Reaction equation

HRID 79274 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9]O)=[CH:7][CH:6]=[C:5]([CH3:11])[N:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>ClCCl>[Br:32][CH2:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][C:5]([CH3:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22678477HCID 22678477, compound

Product 1

HCID 672536903-(Bromomethyl)-2-methoxy-6-methylpyridineYield 30.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-methoxy-6-methylpyridin-3-yl)methanol (4.7 g, 30.7 mmol) in dichloromethane (150 mL) was added triphenylphosphine (12.1 g, 46.0 mmol). The mixture was cooled in an ice bath with stirring under an atmosphere of nitrogen. Carbon tetrabromide (15.3 g; 46.0 mmol) was added and the mixture was stirred for 90 minutes. The mixture was concentrated under reduced pressure and purified using column chromatography on silica, eluting with dichloromethane/hexanes (1:1) to give 3-(bromomethyl)-2-methoxy-6-methylpyridine (2.0 g).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. stirringthe mixture was stirred for 90 minutes
  3. concentrationThe mixture was concentrated under reduced pressure
  4. custompurified
  5. washeluting with dichloromethane/hexanes (1:1)

Sources & evidence

ORD record
ord-465f2463928a465a9694a89a9c7541e9
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

Loading…