Benzene → Trichloro(triphenylmethyl)silane

HRID 377053Notes

Reaction equation

HRID 377053 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:12]([Si:15]([Cl:18])([Cl:17])[Cl:16])(Cl)Cl>>[C:1]1([C:12]([Si:15]([Cl:18])([Cl:17])[Cl:16])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 87297Silane, trichloro(trichloromethyl)-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 19360817Trichloro(triphenylmethyl)silaneYield 19%

Procedure

In the same apparatus and procedures as EXAMPLE 2 above, 22.88 ml (256 mmol) of benzene and 0.80 g (6.0 mmol) of aluminum chloride were alkylated with 9.04 g (17.2 mmol) of (trichloromethyl)trichlorosilane under dry nitrogen atmospheric pressure for 1 hr at 50° 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 and benzene were distilled, recrystallization from chloroform yielded 1.23 g of (triphenylmethyl)trichlorosilane (mp; 195-7: E, yield; 19%).

Workup

  1. customfor 1 hr
  2. customat 50° C
  3. customThe aluminum chloride catalyst was quenched with POCl3
  4. additionFreshly distilled hexane(50 ml) was added to the reaction mixture and insoluble solids in hexane
  5. filtrationwere filtered from the organic soultion
  6. distillationAfter hexane and benzene were distilled
  7. customrecrystallization from chloroform

Sources & evidence

ORD record
ord-03e8c84aa05a4d018ef1f412d51fc474
Source dataset
uspto-grants-2000_02
Patent number
US06022987

Reaction notes

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