반응 #64914

반응 방정식

Dimethyl 4-nitrohomophthalate

sodium hydride

2-bromobenzaldehyde

→

off-white product

수율 70.1%

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

수율 70.1%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting solution was stirred for 5-10 min
2. 2
   기타The 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
   추출extracted with dichloromethane (2×)
6. 6
   세척washed with water and brine
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   여과filtered
9. 9
   기타evaporated
10. 10
    기타The residue crystallized

실험 절차

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+).

출처