Réaction #90541

Équation de réaction

PTSA

11

5-bromo-6-methoxy-2,3-dihydro-1H-inden-1-one

4-((trifluoromethyl)thio)benzaldehyde

→

crude compound 104

(E)-5-bromo-6-methoxy-2-(4-((trifluoromethyl)thio)benzylidene)-2,3-dihydro-1H-inden-1-one

Solvants

ethyl acetate

toluene

Conditions de réaction

Traitement

1. 1
   Lavagewashed with water (3×25 mL)
2. 2
   SéchageThe organic layer was dried over sodium sulphate
3. 3
   Concentrationconcentrated

Mode opératoire

To a solution of 11 (250 mg, 1.04 mol) in toluene 15 mL was added 4-((trifluoromethyl)thio)benzaldehyde 72 (235 mg, 1.144 mol). PTSA (357 mg, 2.08 mol) was added, the reaction mixture stirred at 120° C. for 6 h, diluted with ethyl acetate and washed with water (3×25 mL). The organic layer was dried over sodium sulphate and concentrated to get the crude compound 104 and was purified through flash chromatography by using 100-200 mesh silica gel. The resulting compound (E)-5-bromo-6-methoxy-2-(4-((trifluoromethyl) thio)benzylidene)-2,3-dihydro-1H-inden-1-one 104 was eluted at 10% ethyl acetate in hexane to afford yellow coloured solid.

Source