Fluorobenzene → HCID 53719400, compound

HRID 377051Notes

Reaction equation

HRID 377051 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[CH:13]([Si:15]([CH3:18])([Cl:17])[Cl:16])Cl.O=P(Cl)(Cl)Cl>[Cl-].[Al+3].[Cl-].[Cl-].CCCCCC>[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:13]([Si:15]([CH3:18])([Cl:17])[Cl:16])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[F:5]

Participants

7

Reactant 4

HCID 10008FluorobenzeneHCID 24813Phosphorus oxychlorideHCID 73787Silane, dichloro(dichloromethyl)methyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 53719400HCID 53719400, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalystHCID 8058HexaneSolvent2×

Procedure

In a 100 ml, three-necked, frame dried, round bottom flask, aluminum chloride 1.679 (12.5 mmol), fluorobenzene 37.93 ml (404 mmol), and (dichloromethyl)methyldichlorosilane 7.08 ml (50.5 mmol) were reacted for 2 hours as in EXAMPLE 1. The aluminum chloride catalyst was quenched with POCl3 1.15 ml (12.5 mmol) and then stirred for another 1 hour to complete the deactivation. Freshly distilled hexane (50 ml) was added to the reaction mixture and insoluble solids in hexane were filtered from the organic solution. After hexane and fluorobenzene were distilled, the reaction products were vacuum distilled to give 10.49 g of [bis(fluorophenyl)methyl]methyldichlorosilane as a mixture of isomers (bp; 103° C./0.2 torr, yield; 65%).

Workup

  1. customIn a 100 ml, three-necked, frame dried
  2. filtrationwere filtered from the organic solution
  3. distillationAfter hexane and fluorobenzene were distilled
  4. distillationdistilled

Sources & evidence

ORD record
ord-97bd4a72bb3a479f9f8058ef444b5a54
Source dataset
uspto-grants-2000_02
Patent number
US06022987

Reaction notes

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