반응 #887

반응 방정식

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

sodium 4-methyl phenoxide

4-methylphenol

→

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

용매

THF

THF

반응 조건

후처리

1. 1
   기타was removed under reduced pressure
2. 2
   workup.ADDITIONThe residue was treated with water
3. 3
   여과the solid was filtered
4. 4
   세척washed with water
5. 5
   건조dried (Na2SO4)
6. 6
   workup.DISSOLUTIONdissolved in chloroform
7. 7
   세척The chloroform solution was passed through a silica column (elution with 2-5% ether in hexane)

실험 절차

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+).

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