Reaction #487542

Reaction equation

water

methyl 4-amino-2-hydroxybenzoate

1-bromo-3-chloropropane

CESIUM CARBONATE

→

methyl 4-amino-2-(3-chloropropoxy)benzoate

Yield 94.2%

Solvents

DMF

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   Washwashed with brine
3. 3
   Dryingdried over MgSO4
4. 4
   Concentrationconcentrated
5. 5
   OtherThe crude product was purified by silica gel chromatography

Procedure

To a solution of methyl 4-amino-2-hydroxybenzoate (500 mg, 2.99 mmol) and 1-bromo-3-chloropropane (0.294 mL, 2.99 mmol) in DMF (3 mL) was added CESIUM CARBONATE (1462 mg, 4.49 mmol). The resulting mixture was stirred at 60° C. for 6 hrs. The reaction mixture was poured into water, extracted with ethyl acetate, washed with brine, dried over MgSO4, concentrated. The crude product was purified by silica gel chromatography using a gradient of 20-50% EtOAc/Hexanes to give 686 mg (94%) methyl 4-amino-2-(3-chloropropoxy)benzoate.

Source