Reaction #1355837

Reaction equation

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

2-bromopyridine

K2CO3

dimethoxyethane

→

2-(2-hydroxyphenyl)pyridine

Yield 80.1%

Solvents

water

Conditions

Workup

1. 1
   TemperatureThe mixture was heated
2. 2
   Temperatureto reflux for 24 hours under nitrogen
3. 3
   ExtractionThe reaction mixture was extracted with ethyl acetate
4. 4
   Otherthe organic phase was separated on silica gel column with 15% ethyl acetate
5. 5
   Washas elute solvent

Procedure

9.5 g (˜43 mmol) of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 6.8 g (˜43 mmol) of 2-bromopyridine, 1.5 g (1.3 mmol) of Pd(PPh3)4, and 16 g (116 mmol) of K2CO3 were added to a 250 mL round bottle flask, along with a solvent mixture of 120 mL of dimethoxyethane and 150 mL of water. The mixture was heated to reflux for 24 hours under nitrogen. The reaction mixture was extracted with ethyl acetate and the organic phase was separated on silica gel column with 15% ethyl acetate as elute solvent. ˜5.9 g (yield ˜80%) of 2-(2-hydroxyphenyl)pyridine was obtained as a colorless liquid.

Source