反応 #887

反応方程式

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

sodium 4-methyl phenoxide

4-methylphenol

→

1-(4-tolyloxyl)-1,2-bis(4-bromobenzoyl)ethylene

溶媒

THF

THF

反応条件

後処理

1. 1
   その他was removed under reduced pressure
2. 2
   workup.ADDITIONThe residue was treated with water
3. 3
   ろ過the solid was filtered
4. 4
   洗浄washed with water
5. 5
   乾燥dried (Na2SO4)
6. 6
   workup.DISSOLUTIONdissolved in chloroform
7. 7
   洗浄The chloroform solution was passed through a silica column (elution with 2-5% ether in hexane)

実験手順

To a solution of 1,2-dibromo-1,2-di(4-bromobenzoyl) ethane (11.1 g, 0.02 mole) in 35 ml of THF was added a suspension of sodium 4-methyl phenoxide [prepared from 0.92 g (0.04 mole) Na and 4.32 g (0.04 mole) 4-methylphenol in 30 ml THF by refluxing for 4-5 hr]. The yellow mixture was refluxed for 2-3 hr (TLC followed) after which the THF was removed under reduced pressure. The residue was treated with water, and the solid was filtered, washed with water, dried (Na2SO4), and dissolved in chloroform. The chloroform solution was passed through a silica column (elution with 2-5% ether in hexane). The result was an off white crystalline solid, 4.95 g (50%), mp 137°-8° C. IR (KBr) 3087, 3035, 2868, 1687, 1646, 1587, 1572, 1557, 1502, 1399, 1364, 1194, 1068, 1009, 971, 876, 815, 772, 526. 1H NMR (CDCl3 /35° C.) 7.92 (d, 2H, J=8.8), 7.65 (d, 2H, J=8.8), 7.55 (d, 2H, J=8.8), 7.48 (d, 2H, J=8.8), 7.27 (d, 2H, J=8.3), 7.11 (d, 2H, J=8.3), 6.32 (s, 1H), 2.4 (s, 3H). 13C NMR (CDCl3 /35° C.) 189.4, 187.6, 168.4, 150.9, 136.6, 136.0, 133.4, 132.3, 131.8, 130.9, 130.3, 129.6, 129.2, 128.2, 120.6, 101.8, 20.95. MS m/e 500 (M+).

出典