1,4-Dichlorobenzene → HCID 19360813, compound
Reaction equation
[Cl-:1].[Al+3].[Cl-:3].[Cl-].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.Cl[CH:14]([Si:16]([CH3:19])([Cl:18])[Cl:17])Cl.O=P(Cl)(Cl)Cl>[Cl-].[Al+3].[Cl-].[Cl-].CCCCCC>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[CH:14]([Si:16]([CH3:19])([Cl:18])[Cl:17])[C:6]1[CH:11]=[C:10]([Cl:1])[CH:9]=[CH:8][C:7]=1[Cl:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 150 °C
Procedure
To a 250 ml, three-necked, frame dried, round bottom flask equipped with a magnetic stirrer, a reflux condenser, and a dropping funnel, aluminum chloride 1.28 g (9.60 mmol) and 1,4-dichlorobenzene 62.89 g (428 mmol) were placed under dry nitrogen atmospheric pressure. After (dichloromethyl) methyldichlorosilane 14.12 g (72.31 mmol) was added to the solution, the reaction mixture was heated for 7 hours at 150° C. The aluminum chloride catalyst was quenched with POCl3 1.47 g (9.59 mmol) and then stirred for another 1 hour 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 soultion. After hexane was distilled, the reaction products were vacuum distilled at 0.2 torr to give 14.14 g of [bis(2,5-dichlorophenyl)methyl] methyldichlorosilane (bp; 154° C./0.2 torr, yield; 47%).
Workup
- customTo a 250 ml, three-necked, frame dried
- customround bottom flask equipped with a magnetic stirrer, a reflux condenser, and a dropping funnel
- filtrationwere filtered from the organic soultion
- distillationAfter hexane was distilled
- distillationdistilled at 0.2 torr
Sources & evidence
- ORD record
- ord-6eeea1c50dd64498bdbc91225f48734c
- Source dataset
- uspto-grants-2000_02
- Patent number
- US06022987
Reaction notes
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