Reaction #45606

Reaction equation

2-Amino-5-bromo-4-fluoro-3-hydroxy-6-methylbenzonitrile

diisopropylethylamine

cyclopropanecarbonyl chloride

→

compound

Yield 97.3%

2-Amino-5-bromo-3-cyano-6-fluoro-4-methylphenyl acetate

Yield 97.3%

Solvents

ethyl acetate

ethyl acetate

Conditions

Workup

1. 1
   workup.ADDITIONwas added to the reaction liquid
2. 2
   Washby washing with water and saturated brine
3. 3
   ConcentrationThe organic layer was concentrated under reduced pressure
4. 4
   Otherthe resulting residue was recrystallized with diisopropyl ether/ethyl acetate

Procedure

2-Amino-5-bromo-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-75) (7.86 g, 32.08 mmol) and diisopropylethylamine (19.5 ml, 112.2 mmol) were dissolved in ethyl acetate (300 ml), and at 0° C., cyclopropanecarbonyl chloride (4.4 ml, 48.12 mmol) was dropwise added, followed by stirring at room temperature for 16 hours under nitrogen atmosphere. After the reaction, ethyl acetate was added to the reaction liquid, followed by washing with water and saturated brine. The organic layer was concentrated under reduced pressure, the resulting residue was recrystallized with diisopropyl ether/ethyl acetate to obtain the entitled compound (8.96 g, 89%) as a white solid.

Source