Sodium Carbonate → 9-(3-Bromophenyl)phenanthrene

HRID 1827603ノート

反応式

HRID 1827603 の反応式
[Br:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][CH:7]=1.[C:9]1(B(O)O)[C:22]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:21]2[C:22]3[C:13]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[CH:20]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 10082252Phenanthreneboronic acid

生成物 1

HCID 221380359-(3-Bromophenyl)phenanthrene収率 85%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Under an atmosphere of argon, 3-bromoiodobenzene (7.0 g, 25 mmole), phenanthreneboronic acid (5.0 g, 23 mmole) and tetrakis-(triphenylphosphine)palladium(0) (0.5 g, 0.43 mmole, 1.7% Pd) were dissolved into toluene (100 ml). To the obtained solution, an aqueous solution of sodium carbonate (7.3 g, 69 mmole, 3 eq/35 ml) was added and the resultant solution was heated under refluxing for 10 hours and left standing for one night. The formed organic layer was separated, washed with a saturated aqueous solution of sodium chloride (50 ml) and dried with anhydrous magnesium sulfate. Then, the solvent was removed by distillation and a yellow oil was obtained. The obtained oil was purified by the column chromatography (silica gel/hexane, hexane+3% dichloromethane and hexane+5% dichloromethane, successively) and white needle crystals (6.5 g, 85%) were obtained.

後処理

  1. temperatureunder refluxing for 10 hours
  2. waitleft
  3. waitstanding for one night
  4. customThe formed organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride (50 ml)
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThen, the solvent was removed by distillation
  8. customa yellow oil was obtained
  9. customThe obtained oil was purified by the column chromatography (silica gel/hexane, hexane+3% dichloromethane and hexane+5% dichloromethane

出典と根拠

ORDレコード
ord-4408a0ae10d64655b0965289086c886b
出典データセット
uspto-grants-2006_05
特許番号
US07053255B2

反応ノート

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