Réaction #889

Équation de réaction

KBr

1,2-dibromo-1,2-di(4-bromobenzoyl) ethane

sodium methoxide

→

1,2-Bis(4-bromobenzoyl)-1-methoxyethane

Solvants

methanol

methanol

Conditions de réaction

Traitement

1. 1
   TempératureThe yellow brown mixture was refluxed for 1-1.5 hr
2. 2
   AutreThe solvent was removed by distillation
3. 3
   Extractionthe mixture was extracted with 100 mL chloroform
4. 4
   ExtractionThe chloroform extract
5. 5
   Lavagewas washed with water
6. 6
   Séchagedried (Na2SO4)
7. 7
   Concentrationconcentrated
8. 8
   AutreThe residue obtained
9. 9
   Autreto yield off-white crystalline solid, 6.6 g (78%), mp 153°-154° C

Mode opératoire

To a solution of 1,2-dibromo-1,2-di(4-bromobenzoyl) ethane (11.1 g, 0.02 mole) in 150 mL dry methanol was added a solution of sodium methoxide in methanol (0.92 g sodium in 50 mL methanol). The yellow brown mixture was refluxed for 1-1.5 hr. The solvent was removed by distillation, the residue was suspended in water and the mixture was extracted with 100 mL chloroform. The chloroform extract was washed with water, dried (Na2SO4) and concentrated. The residue obtained was titrated with dry methanol-ether (3:1) to yield off-white crystalline solid, 6.6 g (78%), mp 153°-154° C. IR (KBr): 3106, 3062, 2932, 1689, 1649, 1583, 1556, 1403, 1223, 1202, 1182, 1086, 1010, 1000, 857, 814, 738, 618, 472 cm-1. 1H (DMSO-d6 /40° C.): 7.95 (d, 2H, J=7.8), 7.77 (4H, J=8.8), 7.72 (d, 2H, J=7.8), 6.89 (s, 1H), 4.03 (s, 3H). 13C (DMSO-d6 /40° C.): 189.9, 187.2, 168.8, 139.9, 135.9, 133.1, 132.2, 131.8, 130.3, 128.1, 127.4, 98.6, 58.5. MS m/e 424 (M+).

Source