Reaction #1806912

Reaction equation

1-chloroethyl 5-(2,4-difluorophenyl)salicylate

sodium ethyl carbonate

→

1-(ethoxycarbonyloxy)ethyl 5-(2,4-difluorophenyl)salicylate

Solvents

DMF

Conditions

Workup

1. 1
   Concentrationconcentrated in vacuo
2. 2
   OtherThe concentrate is partitioned between ether/ethyl acetate
3. 3
   OtherThe organic layer is separated
4. 4
   Extractionthe aqueous layer is again extracted with ether
5. 5
   Washwashed with water
6. 6
   Otherby drying
7. 7
   Concentrationconcentration to the crude product
8. 8
   OtherAfter further purification by chromatography
9. 9
   Otherthe product is crystallized from hexane

Procedure

To a solution of 1-chloroethyl 5-(2,4-difluorophenyl)salicylate (5.0 g) in about 40 ml of DMF is added portionwise 3.0 g of sodium ethyl carbonate. The reaction is stirred at room temperature and then concentrated in vacuo. The concentrate is partitioned between ether/ethyl acetate and acidified water. The organic layer is separated and the aqueous layer is again extracted with ether, the organic layers are pooled and washed with water followed by drying and concentration to the crude product. After further purification by chromatography as described in Example 1, the product is crystallized from hexane to afford pure 1-(ethoxycarbonyloxy)ethyl 5-(2,4-difluorophenyl)salicylate.

Source