Réaction #91896

Équation de réaction

H2SO4

H2SO4

7-bromochroman-4-one

AlCl3

TMSCN

→

crude title compound

Rendement 45.0%

7-bromo-2H-chromene-4-carboxamide

Rendement 45.0%

Solvants

H2O

AcOH

toluene

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was cooled to rt
2. 2
   TempératureThe reaction was heated to 130° C.
3. 3
   workup.STIRRINGstirred for 6 h
4. 4
   TempératureThe reaction was cooled
5. 5
   Filtrationfiltered
6. 6
   workup.DISSOLUTIONThe filter cake dissolved in THF (50 mL)
7. 7
   Filtrationfiltered
8. 8
   ConcentrationThe combined organic solutions were concentrated

Mode opératoire

To a solution of 7-bromochroman-4-one (2.0 g, 8.8 mmol) and AlCl3 (118 mg, 0.9 mmol) in toluene (10 mL) was added TMSCN (1.3 mL, 9.7 mmol). The solution was stirred at 40° C. for 1.5 h. The reaction was cooled to rt, and H2SO4 (1.0 mL) was added, followed by AcOH (13 mL) and more H2SO4 (4.3 mL). The reaction was heated to 130° C. and stirred for 6 h. The reaction was cooled, poured over H2O (100 mL) and filtered. The filter cake dissolved in THF (50 mL) and filtered. The combined organic solutions were concentrated to give 1.0 g (45%) of the crude title compound as an off-white solid. [M+H] calc'd for C10H8BrNO2, 254, 256. found 254, 256.

Source