Réaction #74496

Équation de réaction

4-bromo-1-hydroxy-2-naphthoic acid

compound 67

4-bromo-1-hydroxy-2-naphthoic acid

dimethyl sulfate

K2CO3

→

title compound

Rendement 78.6%

Methyl 4-bromo-1-methoxy-2-naphthoate

Rendement 78.6%

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   Températurewas refluxed overnight
2. 2
   FiltrationThe solid was filtered
3. 3
   Autrecondensed
4. 4
   Autreto give a solid residue, which
5. 5
   Autrewas recrystallized from EtOAc/hexanes

Mode opératoire

A mixture of 4-bromo-1-hydroxy-2-naphthoic acid (compound 67, 24.7 g, 92.2 mmol), dimethyl sulfate (21.8 mL, 231 mmol), and K2CO3 (31.9 g, 231 mmol) in acetone (200 mL) was refluxed overnight. The solid was filtered, and the filtrate was condensed to give a solid residue, which was recrystallized from EtOAc/hexanes to afford the title compound (21.4 g, 78%) as a white solid.

Source