Biphenyl → HCID 11129642, compound

HRID 1457370Notes

Reaction equation

HRID 1457370 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl[CH:18]([Si:20]([CH3:23])([Cl:22])[Cl:21])Cl.O=P(Cl)(Cl)Cl>[Cl-].[Al+3].[Cl-].[Cl-].CCCCCC>[CH3:18][Si:20]([Cl:22])([Cl:21])[CH:23]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:5]2[C:10]1=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

7

Reactant 4

HCID 7095BiphenylHCID 24813Phosphorus oxychlorideHCID 73787Silane, dichloro(dichloromethyl)methyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 11129642HCID 11129642, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalystHCID 8058HexaneSolvent2×

Procedure

To a 100 ml, three-necked, frame dried, round bottom flask equipped with a magnetic stirrer, a reflux condenser, and a dropping funnel, aluminum chloride 1.43 g (10.7 mmol) and biphenyl 16.5 g (107 mmol) were placed under dry nitrogen atmospheric pressure. After (dichloromethyl)methyldichlorosilane 7.50 ml (53.5 mmol) was added to the solution, the reaction mixture was heated for 2.5 hrs. at 120° C. The aluminum chloride catalyst was quenched with POCl3 1.04 ml (11.2 mmol) and then stirred for another 1 hr. to complete the deactivation. Freshly distilled hexane (100 ml) was added to the reaction mixture and insoluble solids in hexane were filtered from the organic solution. After hexane was distilled, the reaction products were vacuum distilled at 0.2 torr to give 8.79 g of 9-(methyldichlorosilyl)fluorene (bp; 115°-120° C./0.2 torr, yield; 59%).

Workup

  1. customTo a 100 ml, three-necked, frame dried
  2. customround bottom flask equipped with a magnetic stirrer, a reflux condenser, and a dropping funnel
  3. temperaturethe reaction mixture was heated for 2.5 hrs
  4. customat 120° C
  5. filtrationwere filtered from the organic solution
  6. distillationAfter hexane was distilled
  7. distillationdistilled at 0.2 torr

Sources & evidence

ORD record
ord-8048e98e56424bcf9cef3f14c1838a1b
Source dataset
uspto-grants-1998_12
Patent number
US05847182

Reaction notes

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