Carbon tetrabromide → 5-(Bromomethyl)-2,3-dichloropyridine

HRID 730866Notes

Reaction equation

HRID 730866 reaction equation
[C:1]([Br:5])(Br)(Br)Br.[Cl:6][C:7]1[CH:8]=[C:9](CO)[CH:10]=[N:11][C:12]=1[Cl:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CC#N>[Br:5][CH2:1][C:9]1[CH:8]=[C:7]([Cl:6])[C:12]([Cl:13])=[N:11][CH:10]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21882961(5,6-Dichloropyridin-3-yl)methanol

Product 1

HCID 219623285-(Bromomethyl)-2,3-dichloropyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

CBr4 (497 mg, 1.5 mmol, Aldrich) was added portionwise to a solution of (5,6-dichloro-pyridin-3-yl)-methanol (178 mg, 1.0 mmol, TCI-US) and PPh3 (393 mg, 1.5 mmol, Aldrich) in CH3CN (3 mL) with stirring at room temperature. The mixture was stirred at room temperature for 30 min, the solvent was removed in vacuo and the residue was purified by silica gel column chromatography, eluting with 10% EtOAc/hexane to give the title compound. MS (ESI, pos. ion) m/z: 242 (M+1).

Workup

  1. stirringThe mixture was stirred at room temperature for 30 min
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified by silica gel column chromatography
  4. washeluting with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-cf1bb4c324fb453faa78502d11a388b7
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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