Reaction #4021

Reaction equation

2-Amino-4-bromophenol

2-chloro-1,1,1-triethoxyethane

water

→

2-Chloromethyl-5-bromobenzoxazole

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureThe resulting solution was warmed on a steambath for 1.5 hour
2. 2
   OtherThe precipitated solid was collected
3. 3
   Otherair-dried
4. 4
   Otherto obtain the product (1.12 g

Procedure

2-Amino-4-bromophenol (1.6 g) prepared according to U.S. Pat. No. 4,157,444 was dissolved in ethanol (5 ml) and 2-chloro-1,1,1-triethoxyethane (1.9 g) was added. The resulting solution was warmed on a steambath for 1.5 hour. After cooling the reaction mixture to room temperature, cold water (5 ml) was added. The precipitated solid was collected and air-dried to obtain the product (1.12 g; m.p. 63°-65° C.

Source