Benzyl Alcohol → 2-Benzyloxy-6-bromopyridine

HRID 1109724Notes

Reaction equation

HRID 1109724 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[CH2:9]([OH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:9]([O:16][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 244Benzyl AlcoholHCID 122742,6-Dibromopyridine

Product 1

HCID 8174752-Benzyloxy-6-bromopyridineYield 76%

Procedure

2,6-Dibromopyridine was condensed with benzyl alcohol by Ullmann reaction to obtain 2-benzyloxy-6-bromopyridine (yield 76%). This was further condensed with m-cresol by Ullmann reaction to obtain 2-benzyloxy-6-(3-methylphenoxy)-pyridine (yield 83%), which was then subjected to catalytic reduction in the presence of a catalyst, 5% palladium-carbon, to obtain 6-(3-methylphenoxy)-2-pyridone (yield 96%).

Workup

  1. customby Ullmann reaction

Sources & evidence

ORD record
ord-51cb2f199786405ca003de1b23808b24
Source dataset
uspto-grants-1994_06
Patent number
US05322845

Reaction notes

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