2-Bromo-9-fluorenone → 9-(2-Biphenylyl)-2-bromo-9-fluorenol

HRID 1433176Notes

Reaction equation

HRID 1433176 reaction equation
[Mg].[Br:2][C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=1>BrC(Br)C.C(OCC)C>[C:12]1([C:13]2[CH:5]=[CH:4][CH:3]=[CH:15][CH:14]=2)[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[C:6]1([OH:16])[C:5]2[CH:4]=[C:3]([Br:2])[CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2

Participants

5

Reactant 2

HCID 7258312-Bromo-9-fluorenoneHCID 5462224Magnesium

Product 1

HCID 225643739-(2-Biphenylyl)-2-bromo-9-fluorenol

Reagents, catalysts & solvents 2

HCID 112011,1-DibromoethaneCatalystHCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
50 °C

Procedure

1.3 g (52 mmol) of magnesium was put into a 200 mL three-neck flask and stirred for 0.5 hours while reducing pressure with a rotary pump. Then, under a nitrogen gas stream, 5.0 mL of diethyl ether and one drop of dibromoethane were added. A solution in which 12 g (50 mmol) of 2-bromophenyl was dissolved in 15 mL of diethyl ether was dropped into this mixture at a pace that maintained reflux flow. After completion of dropping, the reaction mixture was refluxed at 50° C. for 3 hours so as to become a Grignard reagent. 12 g (45 mmol) of 2-bromo-9-fluorenone was put into a 200 mL three-neck flask, and after nitrogen substitution in the flask was carried out, 40 mL of diethyl ether was added into the flask. The synthesized Grignard reagent was dropped into this solution, and after completion of dropping, the solution was refluxed at 50° C. for 3 hours, and then stirred at room temperature for 24 hours. After completion of a reaction, the reaction solution was washed with water, and a water layer was extracted with ethyl acetate. The extracted solution and an organic layer were combined and washed with saturated saline, and then dried with magnesium sulfate. After drying, this mixture was subjected to suction filtration, and when a filtrate was concentrated, 19 g of a light yellow, powdery solid of 9-(biphenyl-2-yl)-2-bromofluoren-9-ol that was a target matter was obtained with the yield of 91%.

Workup

  1. additionwas dropped into this mixture at a pace that
  2. temperaturemaintained
  3. temperaturereflux flow
  4. temperaturethe solution was refluxed at 50° C. for 3 hours
  5. stirringstirred at room temperature for 24 hours
  6. customAfter completion of a reaction
  7. washthe reaction solution was washed with water
  8. extractiona water layer was extracted with ethyl acetate
  9. washwashed with saturated saline
  10. dry with materialdried with magnesium sulfate
  11. customAfter drying
  12. filtrationthis mixture was subjected to suction filtration, and when a filtrate
  13. concentrationwas concentrated
  14. customwas obtained with the yield of 91%

Sources & evidence

ORD record
ord-c0476493ed664bdda9e2a80cba9e71fd
Source dataset
uspto-grants-2009_11
Patent number
US07612204B2

Reaction notes

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