Reaction #50475

Reaction equation

methyl 4-chlorosalicylate

methyl 3-bromopropionate

potassium carbonate

→

desired material

Yield 102.6%

4- Chloro-2-(2-methoxy-1-methyl-2-oxoethoxy)benzoic acid, methyl ester

Yield 102.6%

Solvents

dimethyl formamide

water

Conditions

Workup

1. 1
   ExtractionThe mixture was extracted with ether
2. 2
   Washthe organics were washed with water
3. 3
   OtherThe organic layer was dried
4. 4
   Otherevaporated

Procedure

A solution of methyl 4-chlorosalicylate (5.0 g) in dimethyl formamide (10 ml) was treated sequentially with methyl 3-bromopropionate (4.0 g) and potassium carbonate (6.0 g). The mixture was stirred at room temperature for 18 hrs and diluted with water. The mixture was extracted with ether and the organics were washed with water. The organic layer was dried and evaporated to give the desired material (6.7 g) as a low melting solid. NMR: 7.8 (d, 1H), 7.2 (m 1H), 6.9 (m, 1H), 4.8 (q, 1H), 3.9 (s, 3H), 3.8 (s, 3H), 1.7 (d, 3H).

Source