Potassium Iodide → 2-Bromo-9,10-bis(4-fluorophenyl)anthracene

HRID 2243460ノート

反応式

HRID 2243460 の反応式
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)(O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)(O)[C:4]=2[CH:3]=1.[I-].[K+].O.[PH2](=O)[O-].[Na+].[PH2](=O)O>C(O)(=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:6]3[C:11]([C:12]=2[C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 4124402Phosphinic AcidHCID 592111502-Bromo-9,10-bis(4-fluorophenyl)-9,10-dihydro-9,10-anthracenediolHCID 178418950HCID 178418950、化合物

生成物 1

HCID 592111052-Bromo-9,10-bis(4-fluorophenyl)anthracene収率 93.5%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
120 °C

実験手順

8.32 g (17.3 mmol) of 2-bromo-9,10-bis(4-fluorophenyl)-9,10-dihydro-9,10-anthracenediol, 5.17 g (31.1 mmol) of potassium iodide, 9.90 g (93.4 mmol) of sodium phosphinate monohydrate, and 50 mL of glacial acetic acid were put into a 200 mL three-neck flask, and the mixture was refluxed at 120° C. for 4 hours. Then, 20 mL of a 50% phosphinic acid was added into the reaction mixture, and the mixture was stirred for 1 hour at 120° C. After the reaction, the reaction mixture was washed with water, and the aqueous layer was extracted with ethyl acetate. This extracted solution was combined with the organic layer, and then dried with magnesium sulfate. After drying, the mixture was subjected to suction filtration, and the filtrate was concentrated. The obtained residue was dissolved in toluene, and filtered through Florisil, celite, and then alumina, and the filtrate was concentrated. The obtained residue was recrystallized with chloroform and hexane, giving 7.2 g of 2-bromo-9,10-bis(4-fluorophenyl)anthracene as light yellow powder in 74% yield.

後処理

  1. customAfter the reaction
  2. washthe reaction mixture was washed with water
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialdried with magnesium sulfate
  5. customAfter drying
  6. filtrationthe mixture was subjected to suction filtration
  7. concentrationthe filtrate was concentrated
  8. dissolutionThe obtained residue was dissolved in toluene
  9. filtrationfiltered through Florisil, celite
  10. concentrationalumina, and the filtrate was concentrated
  11. customThe obtained residue was recrystallized with chloroform and hexane

出典と根拠

ORDレコード
ord-ed36d381bdfb4453b7d7ece83d58fc49
出典データセット
uspto-grants-2010_03
特許番号
US07674914B2

反応ノート

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