Benzoyl Peroxide → 4-(Bromomethyl)-2,6-di-tert-butylpyridine

HRID 398054Notes

Reaction equation

HRID 398054 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[N:13]=1)[C:8](O)=O)([CH3:4])([CH3:3])[CH3:2].C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.[Br:33]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[Br:33][CH2:8][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[N:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:11]=1

Participants

5

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 47369412,6-Di-tert-butylisonicotinic acid2×

Product 1

HCID 129308884-(Bromomethyl)-2,6-di-tert-butylpyridine

Procedure

Reaction Scheme 13 provides an example for the preparation of 2,6-di-tert-butylisonicotinic acid (Compound C3) which is a reagent in accordance with Formula 8 for the preparation of several preferred compounds of the present invention. Thus, 2,6-di-tert-butyl-4-methylpyridine (available commercially from Aldrich Chemical Co.) is reacted with N-bromosuccinimide and benzoyl peroxide to provide 4-bromomethyl-2,6-di-tert-butylpyridine (Compound A3). Compound A3 is reacted with base (sodium hydroxyde) to yield the coresponding hydroxymethyl compound (Compound B3), which is thereafter oxidized in a Jones oxidation reaction to give 2,6-di-tert-butylisonicotinic acid (Compound C3).

Workup

  1. customReaction Scheme 13
  2. customprovides an example
  3. customfor the preparation of several preferred compounds of the present invention

Sources & evidence

ORD record
ord-d089d323fb034f3f9e95f92fdb4787d6
Source dataset
uspto-grants-2003_08
Patent number
US06610744B2

Reaction notes

Loading…