对甲基苯酚 → 1-(4-Tolyloxy)-1,2-bis-(4-bromobenzoyl)ethylene

HRID 791

反应方程式

HRID 791 反应方程式
Br[CH:2]([C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)[CH:3](Br)[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1.[CH3:23][C:24]1[CH:30]=[CH:29][C:27]([O-:28])=[CH:26][CH:25]=1.[Na+].CC1C=CC(O)=CC=1>C1COCC1>[C:24]1([CH3:23])[CH:30]=[CH:29][C:27]([O:28][C:2]([C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)=[CH:3][C:4](=[O:12])[C:5]2[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=2)=[CH:26][CH:25]=1

参与物

5

反应物 3

HCID 2879对甲基苯酚HCID 117313561,2-Dibromo-1,2-di(4-bromobenzoyl)ethaneHCID 23673456Sodium p-methylphenolate

产物 1

HCID 539578091-(4-Tolyloxy)-1,2-bis-(4-bromobenzoyl)ethylene

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂2 次

实验过程

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+).

后处理

  1. customwas removed under reduced pressure
  2. additionThe residue was treated with water
  3. filtrationthe solid was filtered
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. dissolutiondissolved in chloroform
  7. washThe chloroform solution was passed through a silica column (elution with 2-5% ether in hexane)

来源与证据

ORD记录
ord-523a53f4b10c44568fb08b813772adeb
来源数据集
uspto-grants-1998_03
专利号
US05723288

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