Reaction #1509640

Reaction equation

4-bromobenzoylchloride

2-bromoaniline

Cs2CO3

1,10-phenathroline

→

Compound 27

Yield 87.0%

2-(4-bromophenyl)benzo[d]oxazole

Yield 87.0%

Solvents

1,4-dioxane

Conditions

Workup

1. 1
   Otherwas degassed
2. 2
   TemperatureThe resulting mixture was cooled
3. 3
   workup.ADDITIONpoured into ethyl acetate (˜200 mL)
4. 4
   Filtrationfiltered
5. 5
   OtherThe filtrate was absorbed on silica gel
6. 6
   Otherpurified by column chromatography (hexanes/ethyl acetate 4:1)
7. 7
   Otherprecipitated by hexanes

Procedure

A mixture of 4-bromobenzoylchloride (4.84 g, 22 mmol), 2-bromoaniline (3.8 g, 22 mmol), CuI (0.21 g, 1.1 mmol), Cs2CO3 (14.3 g, 44 mmol) and 1,10-phenathroline (0.398 g, 2.2 mmol) in anhydrous 1,4-dioxane (80 mL) was degassed and the resulting mixture was heated at about 125° C. under argon overnight. The resulting mixture was cooled and poured into ethyl acetate (˜200 mL) and filtered. The filtrate was absorbed on silica gel, purified by column chromatography (hexanes/ethyl acetate 4:1), and precipitated by hexanes to give a white solid (Compound 27) (5.2 g, in 87% yield).

Source