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

HRID 912925Notes

Reaction equation

HRID 912925 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-4fb8987210984b949dd2b84be3962894
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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