Reacción #582508

Ecuación de reacción

methanol

4-bromoacetophenone

methyl 4-bromobenzoic acid

sodium hydride

→

4′-Bromo-2-(4-bromobenzoyl)acetophenone

Disolventes

benzene

—

three

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction
2. 2
   TemperaturaAfter the mixture was refluxed overnight
3. 3
   Otrothe reaction was quenched
4. 4
   workup.ADDITIONby adding methanol
5. 5
   workup.ADDITIONpouring it into ice water
6. 6
   OtroA solid was collected
7. 7
   Lavadowashed with water
8. 8
   Otrorecrystallized from benzene
9. 9
   Otroto give a light yellow product

Procedimiento

In a 1-liter three neck round bottom flask, 43 g (0.2 mol) methyl 4-bromobenzoic acid and 17.6 g (0.4 mol) sodium hydride were dissolved in 200 ml dried benzene and heated to 60° C. Next, 39.8 g (0.2 mol) 4-bromoacetophenone in 100 ml dry benzene was slowly added through a dropping funnel, and 1 ml methanol was added to the flask to initiate the reaction. After the mixture was refluxed overnight, the reaction was quenched by adding methanol and pouring it into ice water. The pH of the mixture was brought down to 7.0 using 5 N sulfuric acid. A solid was collected, washed with water, and recrystallized from benzene to give a light yellow product. Characterization. Yield: 30.3 g (40%). 1H NMR (300 MHz, CDCl3, 20° C., δ): 7.84 (d, 4H, ArH); 7.62 (d, 4H, ArH); 6.77 (s, 2H, CH2). EI-MS: 382(M+), 301, 225, 183, 157.

Fuente