Potassium Bromide → 2,5-bis(4-Bromophenyl)-3-(p-tolyloxy)furan

HRID 234114

反応式

HRID 234114 の反応式
[C:1]1([CH3:28])[CH:6]=[CH:5][C:4]([O:7][C:8]([C:19](=O)[C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)=[CH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)=[CH:3][CH:2]=1.[K+].[Br-]>P(Cl)(Cl)Cl>[Br:26][C:23]1[CH:22]=[CH:21][C:20]([C:19]2[O:18][C:10]([C:11]3[CH:12]=[CH:13][C:14]([Br:17])=[CH:15][CH:16]=3)=[CH:9][C:8]=2[O:7][C:4]2[CH:3]=[CH:2][C:1]([CH3:28])=[CH:6][CH:5]=2)=[CH:25][CH:24]=1

参加物

4

反応物 2

HCID 253877Potassium BromideHCID 539578091-(4-Tolyloxy)-1,2-bis-(4-bromobenzoyl)ethylene

生成物 1

HCID 103452192,5-bis(4-Bromophenyl)-3-(p-tolyloxy)furan

試薬・触媒・溶媒 1

HCID 24387Phosphorus trichloride溶媒

実験手順

A solution of 5.0 g (0.01 mole) 1-(4-tolyloxy)-1,2-bis-(4-bromobenzoyl) ethylene in 10 ml phosphorus trichloride was heated under reflux for 3-4 hr (TLC followed). The excess PCl3 was removed by distillation and the residue was triturated with ice/water (exothermic reaction). The solution was extracted with dichloromethane (75 ml) and the dichloromethane layer was washed with saturated sodium bicarbonate solution, water, and dried (Na2SO4). The solvent was removed under reduced pressure. The residual solid was chromatographed over silica gel using ether:hexane (2:8 to 1:1) as eluant. An off white crystalline solid was obtained, 2.78 g (56%), mp 92°-3° C. IR (KBr) 2923, 2851, 1560, 1506, 1467, 1390, 1209, 1072, 1066, 945, 825, 707, 486. 1H NMR (CDCl3 /35° C.) 7.69 (d, 2H, J=8.8), 7.46-7.43 (m, 6H), 7.12 (d, 2H, J=8.3), 7.0 (d, 2H, J=8.3), 6.47 (s, 1H), 2.31 (s, 3H). 13C NMR (CDCl3 /135° C.) 150.8, 150.1, 142.8, 139.3, 133.0, 131.9, 131.7, 130.3, 129.1, 128.6, 125.1, 125.0, 121.8, 120.5, 117.1, 102.7, 20.6. MS m/e 484 (M+).

後処理

  1. temperatureunder reflux for 3-4 hr (TLC followed)
  2. customThe excess PCl3 was removed by distillation
  3. customthe residue was triturated with ice/water (exothermic reaction)
  4. extractionThe solution was extracted with dichloromethane (75 ml)
  5. washthe dichloromethane layer was washed with saturated sodium bicarbonate solution, water
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was removed under reduced pressure
  8. customThe residual solid was chromatographed over silica gel
  9. customAn off white crystalline solid was obtained

出典と根拠

ORDレコード
ord-ef0126e38d014dca921edf13e5a1870f
出典データセット
uspto-grants-1997_01
特許番号
US05594138

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