Potassium Iodide → 2-Bromo-9,10-diphenylanthracene

HRID 421527노트

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HRID 421527 반응식
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(O)[C:4]=2[CH:3]=1.[I-].[K+].O.[PH2](=O)[O-].[Na+].[PH2](=O)O>C1(C)C=CC=CC=1.C(O)(=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:6]3[C:11]([C:12]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 4124402Phosphinic AcidHCID 231602182-Bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diolHCID 178418950HCID 178418950, 화합물

생성물 1

HCID 222471632-Bromo-9,10-diphenylanthracene수율 73.3%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 1140Toluene용매

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온도
120 °C

실험 절차

About 7.6 g (17 mmol) of the obtained 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol, 5.1 g (31 mmol) of potassium iodide, 9.7 g (92 mmol) of sodium phosphinate monohydrate, and 50 mL of glacial acetic acid were put into a 500 mL three-neck flask, and the mixture was refluxed at 120° C. for two hours. Thereafter, 30 mL of 50% phosphinic acid was added to the reaction mixture, and the mixture was stirred at 120° C. for one hour. After the reaction, the solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The extract was combined with an organic layer to be dried with magnesium sulfate. After the drying, this mixture was suction filtered, and the obtained filtrate was concentrated to give a solid substance. This solid substance was dissolved in toluene, and the solution was filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina. The obtained filtrate was concentrated to give a solid substance, and the solid substance was recrystallized with a mixed solvent of chloroform and hexane, giving 5.1 g of 2-bromo-9,10-diphenylanthracene, which was the object of the synthesis, as a light yellow powdered solid substance. The yield of the two stages (ii) and (iii) was 74%.

후처리

  1. customAfter the reaction
  2. washthe solution was washed with water
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialto be dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe obtained filtrate was concentrated
  7. customto give a solid substance
  8. filtrationthe solution was filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina
  9. concentrationThe obtained filtrate was concentrated
  10. customto give a solid substance
  11. customthe solid substance was recrystallized with a mixed solvent of chloroform and hexane

출처 및 근거

ORD 기록
ord-be0ffc5411e140429a3b70742b0773ab
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101289B2

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