Reacción #64914

Ecuación de reacción

Dimethyl 4-nitrohomophthalate

sodium hydride

2-bromobenzaldehyde

→

off-white product

Rendimiento 70.1%

Methyl α-[ (2-Bromophenyl)methylene]-(2-carboxy-4-nitrophenyl)acetate

Rendimiento 70.1%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe resulting solution was stirred for 5-10 min
2. 2
   OtroThe cooling bath was removed after 10 min
3. 3
   workup.STIRRINGthe reaction was stirred at room temperature until the mixture
4. 4
   workup.DISSOLUTIONThe solid was dissolved in water
5. 5
   Extracciónextracted with dichloromethane (2×)
6. 6
   Lavadowashed with water and brine
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Otroevaporated
10. 10
    OtroThe residue crystallized

Procedimiento

Dimethyl 4-nitrohomophthalate (Ghosh, C. K.; Mukherjee, K. K. J. Ind. Chem. Soc. 1976, 53, 662) (5 g, 0.02 tool) in THF (20 mL) was added to a suspension of sodium hydride (0.85 g of 60% disp., 0.021 mol) in THF (30 mL) with stirring at 0° C. under nitrogen. The resulting solution was stirred for 5-10 min and 2-bromobenzaldehyde (2.3 mL, 0.02 mol) was added in one portion. The cooling bath was removed after 10 min and the reaction was stirred at room temperature until the mixture solidified. The solid was dissolved in water and extracted with dichloromethane (2×). The aqueous phase was acidified and reextracted 3× with fresh portions of dichloromethane. The latter extracts were combined, washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and evaporated. The residue crystallized on standing to give 5.62 g (70%) of off-white product: 1H NMR (300 MHz, CDCl3) δ 3.90 (3H, s), 6.66 (1H, d), 7.09 (1H, t), 7.16-7.23 (3H, m), 7.69 (1H, d), 7.86 (1H, s), 8.24 (1H, dd), 8.68 (1H, d); MS m/e 423-425 (M+NH4+).

Fuente