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

HRID 79268

Reaction equation

HRID 79268 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:30]>ClCCl>[Br:30][CH2:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 707366-Methyl-2-pyridylmethanol

Product 1

HCID 125437332-(Bromomethyl)-6-methylpyridineYield 66.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled a solution of (6-methylpyridin-2-yl)methanol (400 mg, 3.25 mmol) in dichloromethane (16 mL) under an atmosphere of dry nitrogen was added triphenylphosphine (1278 mg, 4.87 mmol) and carbon tetrabromide (1616 mg, 4.87 mmol). The mixture was stirred for 1 hour. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica, eluting with 2-4% methanol in dichloromethane to give 2-(bromomethyl)-6-methylpyridine as an oil (402 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by chromatography on silica
  3. washeluting with 2-4% methanol in dichloromethane

Sources & evidence

ORD record
ord-c54152b095844a0aa3e78865c3220efb
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Linked notes

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