Reaction #164261

Reaction equation

5-Bromo-2-fluoro-benzoic acid

4-chloro-benzene-1,2-diamine

HATU

water

→

title compound

Yield 52.0%

N-(2-Amino-5-chloro-phenyl)-5-bromo-2-fluoro-benzamide

Yield 52.0%

Solvents

dichloromethane

DMF

Conditions

Workup

1. 1
   workup.WAITleft
2. 2
   workup.WAITstanding at room temperature overnight
3. 3
   Othersolvent removed under reduced pressure
4. 4
   Otherthe crude oil obtained
5. 5
   Otherwas crystallized from the mixture of solvents dichloromethane

Procedure

Method 7—Step a A mixture of 5-Bromo-2-fluoro-benzoic acid (3.00 g, 13.70 mmol), 4-chloro-benzene-1,2-diamine (2.42 g, 16.99 mmol), HATU (5.47 g, 14.38 mmol) and TEA (1.91 mL, 13.83 mmol) in dichloromethane (70 mL) and DMF (16 mL) was stirred at room temperature overnight, then water was added (80 mL) and left standing at room temperature overnight. The organic layer was divided and solvent removed under reduced pressure and the crude oil obtained was crystallized from the mixture of solvents dichloromethane:cyclohexane/3:1 (30 mL) to afford 2.19 g of the title compound (52%).

Source