1,4-Dichlorobenzene → [2,2-Bis(2,5-dichlorophenyl)ethyl]trichlorosilane

HRID 377057

Reaction equation

HRID 377057 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.[Cl-:9].[Al+3].[Cl-:11].[Cl-].Cl[CH:14]([Si:17]([Cl:20])([Cl:19])[Cl:18])[CH2:15]Cl>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:15]([C:2]1[CH:7]=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[Cl:11])[CH2:14][Si:17]([Cl:20])([Cl:19])[Cl:18]

Participants

4

Reactant 3

HCID 46851,4-DichlorobenzeneHCID 79093Silane, trichloro(1,2-dichloroethyl)-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 12127968[2,2-Bis(2,5-dichlorophenyl)ethyl]trichlorosilaneYield 287.3%

Procedure

In the same apparatus and procedures as EXAMPLE 2 above, 17.35 g (118 mmol) of 1,4-dichlorobenzene and 0.47 g (3.5 mmol) of aluminum chloride were alkylated with 5.45 g (23.5 mmol) of (1,2-dichloroethyl)trichlorosilane for 20 min at 120° C. The aluminum chloride catalyst was quenched with POCl3 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 soultion. After hexane was distilled, the reaction products were vacuum distilled to give 4.56 g of [2,2-bis(2,5-dichlorophenyl)ethyl]trichlorosilane (bp; 161-163° C./0.5 torr, yield; 43%).

Workup

  1. customThe aluminum chloride catalyst was quenched with POCl3
  2. additionFreshly distilled hexane (50 ml) was added to the reaction mixture and insoluble solids in hexane
  3. filtrationwere filtered from the organic soultion
  4. distillationAfter hexane was distilled
  5. distillationdistilled

Sources & evidence

ORD record
ord-2cb30ef98a9441a097f67064c95734ae
Source dataset
uspto-grants-2000_02
Patent number
US06022987

Linked notes

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