Reaction #66305

Reaction equation

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

potassium carbonate

chloromethyl ethyl ether

→

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

Yield 84.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureto cool to room temperature
2. 2
   Filtrationfiltered
3. 3
   Concentrationthe filtrate concentrated

Procedure

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (0.50 g, 2.02 mmol) was dissolved in 20 mls of dry acetonitrile. To this solution was added powdered potassium carbonate (0.42 g, 3.02 mmol) followed by chloromethyl ethyl ether (0.24 mls, 2.42 mmol). This mixture was warmed to 65° C. for 2 hours, then allowed to cool to room temperature, filtered and the filtrate concentrated to give ethoxymethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate as a solid (84%). This material was taken onto the next step without further purification.

Source