Réaction #5467

Équation de réaction

water

4-amino-5-chloro-2-hydroxybenzoic acid methyl ester

sodium hydride

2-bromoethyl methyl ether

→

title compound

Rendement 53.0%

4-Amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester

Rendement 53.0%

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was heated to 95°±5° C. for 1.5 hours
2. 2
   Températurecooled
3. 3
   FiltrationThe aqueous suspension was filtered
4. 4
   Lavagethe solid was washed with water, air
5. 5
   Autredried
6. 6
   Autrecollected
7. 7
   Autrerecrystallized from ether/hexane

Mode opératoire

A suspension of 60% sodium hydride/oil dispersion (1.00 g, 25 mmol) in anhydrous dimethylformamide (40 mL) under nitrogen was treated with 4-amino-5-chloro-2-hydroxybenzoic acid methyl ester (4.03 g, 20 mmol), stirred for 30 minutes, then treated with 2-bromoethyl methyl ether (3.48 g, 25 mmol). The mixture was heated to 95°±5° C. for 1.5 hours, then cooled and added to water (250 mL). The aqueous suspension was filtered, and the solid was washed with water, air dried, collected, and recrystallized from ether/hexane to afford 2.75 g (53%) of the title compound; mp 121.0°-122.5° C.

Source