Reaction #657334

Reaction equation

ethyl bromoacetate

4-bromo-2-nitro-phenol

potassium carbonate

→

product

Yield 77.0%

(4-Bromo-2-nitro-phenoxy)-acetic acid ethyl ester

Yield 77.0%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   Temperaturethen cooled to 23° C
2. 2
   OtherThe reaction mixture was partitioned between ethyl acetate:heptane (1:1) and water (100 mL each)
3. 3
   OtherThe organic layer was separated
4. 4
   Washwashed successively with water, saturated brine solution (100 ml
5. 5
   Dryingeach) then dried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated

Procedure

To a solution of 4-bromo-2-nitro-phenol (3.28 g, 15.0 mmol, 1 equiv) in dimethylformamide (40 mL) at 23° C. was added potassium carbonate (4.14 g, 30 mmol, 2 equiv) followed by ethyl bromoacetate (1.84 mL, 16.6 mmol, 1.1 equiv). The resulting mixture was warmed to 60° C. (oil bath) for 90 min then cooled to 23° C. The reaction mixture was partitioned between ethyl acetate:heptane (1:1) and water (100 mL each). The organic layer was separated and washed successively with water, saturated brine solution (100 ml, each) then dried (MgSO4), filtered and concentrated to give 4.50 g (11.5 mmol, 77%) of the product as a yellow oil.

Source