反応 #889

反応方程式

KBr

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

sodium methoxide

→

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

溶媒

methanol

methanol

反応条件

後処理

1. 1
   温度The yellow brown mixture was refluxed for 1-1.5 hr
2. 2
   その他The solvent was removed by distillation
3. 3
   抽出the mixture was extracted with 100 mL chloroform
4. 4
   抽出The chloroform extract
5. 5
   洗浄was washed with water
6. 6
   乾燥dried (Na2SO4)
7. 7
   濃縮concentrated
8. 8
   その他The residue obtained
9. 9
   その他to yield off-white crystalline solid, 6.6 g (78%), mp 153°-154° C

実験手順

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+).

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