Diethyl Ether → 2-(Chloromethyl)-5-phenylpyridine

HRID 1034258Notes

Reaction equation

HRID 1034258 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.CCOCC>C(Cl)(Cl)(Cl)Cl>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][Cl:14])=[N:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 767442-Methyl-5-phenylpyridine

Product 1

HCID 146503502-(Chloromethyl)-5-phenylpyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5-phenyl-2-picoline (6.2 g) in CCl4 (250 mL) were added N-chlorosuccinimide (5.85 g) and benzoylperoxide (100 mg). The reaction was then heated to reflux and irradiated with a 225 watt lamp for 5 hours. After cooling, Et2O was added, the solid filtered and the filtrate was evaporated to dryness. The crude residue was chromatographed on silica gel (hexane/EtOAc 9:1) to give the pure title product.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux
  3. customirradiated with a 225 watt lamp for 5 hours
  4. temperatureAfter cooling
  5. filtrationthe solid filtered
  6. customthe filtrate was evaporated to dryness
  7. customThe crude residue was chromatographed on silica gel (hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-0dddc90d5c1840e5867e77c5dd0d1256
Source dataset
uspto-grants-1994_05
Patent number
US05314898

Reaction notes

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