تفاعل #887

معادلة التفاعل

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

sodium 4-methyl phenoxide

4-methylphenol

→

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

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىwas removed under reduced pressure
2. 2
   workup.ADDITIONThe residue was treated with water
3. 3
   ترشيحthe solid was filtered
4. 4
   غسيلwashed with water
5. 5
   تجفيفdried (Na2SO4)
6. 6
   workup.DISSOLUTIONdissolved in chloroform
7. 7
   غسيلThe chloroform solution was passed through a silica column (elution with 2-5% ether in hexane)

الإجراء التجريبي

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+).

المصدر