Benzoyl Peroxide → 2-(Chloromethyl)-6-(4-fluorophenyl)pyridine

HRID 585174Notes

Reaction equation

HRID 585174 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:3]=1.[Cl:15]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:15][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)[N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 178368152-(4-Fluorophenyl)-6-methylpyridine

Product 1

HCID 223401212-(Chloromethyl)-6-(4-fluorophenyl)pyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

0.60 g (3.2 mmol) of the product of step 2 was dissolved in 50 mL of carbon tetrachloride, along with 0.54 g (3.5 mmol) of N-chloro succinimide and a catalytic amount of benzoyl peroxide. After refluxing for 20 hr, the solution was concentrated and filtered through a plug of silica gel eluting with 20% ethyl acetate:hexane. The resulting oil was contaminated with ˜10% of unreacted starting material and was used in the next step without further purification. NMR (200 MHz, CDCl3) δ 7.96 (m, 2H, ArH), 7.63 (m, 1H, ArH), 7.43 (m, 1H, ArH), 7.17 (m, 3H, ArH), 4.72 (s, 2H, CH2Cl).

Workup

  1. temperatureAfter refluxing for 20 hr
  2. concentrationthe solution was concentrated
  3. filtrationfiltered through a plug of silica gel eluting with 20% ethyl acetate
  4. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-8f5ba84362864e71aed5b0641c186bc8
Source dataset
uspto-grants-2005_08
Patent number
US06930131B2

Reaction notes

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