1,2-Dichlorobenzene → HCID 19360819, compound

HRID 377062Notes

Reaction equation

HRID 377062 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-:9].[Al+3].[Cl-:11].[Cl-:12].Cl[CH:14]([CH:20](Cl)[CH3:21])[CH2:15][Si:16]([Cl:19])([Cl:18])[Cl:17]>>[Cl:9][C:2]1[CH:7]=[C:6]([Cl:11])[CH:5]=[CH:4][C:3]=1[C:20]([C:2]1[CH:3]=[CH:4][C:5]([Cl:12])=[CH:6][C:7]=1[Cl:8])([CH3:21])[CH2:14][CH2:15][Si:16]([Cl:19])([Cl:18])[Cl:17]

Participants

4

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 19360811Trichloro(2,3-dichlorobutyl)silane

Product 1

HCID 19360819HCID 19360819, compoundYield 114.2%

Procedure

In the same apparatus and procedures as EXAMPLE 2 above, 26.3 ml (230 mmol) of 2,3-dichlorobenzene and 1.23 g (9.2 mmol) of aluminum chloride were alkylated with 11.91 g (45.7 mmol) of (2,3-dichlorobutyl)trichlorosilane for 20 min at 90° C. The aluminum chloride catalyst was quenched with POCl3 and then stirred for another 30 min 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, the reaction products were vacuum distilled to give 5.06 g of [3,3-bis(2,4-dichlorophenyl)butyl]trichlorosilane (bp; 186-190° C./0.5 torr, yield; 23%).

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 and benzene were distilled
  5. distillationdistilled

Sources & evidence

ORD record
ord-fe56d8eefea3416eaebcf01ed308094f
Source dataset
uspto-grants-2000_02
Patent number
US06022987

Reaction notes

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