Fluorobenzene → HCID 19360812, compound

HRID 377061Notes

Reaction equation

HRID 377061 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH:13]([CH2:19]Cl)[CH2:14][Si:15]([Cl:18])([Cl:17])[Cl:16]>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:19]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[CH2:13][CH2:14][Si:15]([Cl:18])([Cl:17])[Cl:16]

Participants

4

Reactant 3

HCID 10008FluorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 19360815Trichloro(2,3-dichloropropyl)silane

Product 1

HCID 19360812HCID 19360812, compoundYield 41%

Procedure

In the same apparatus and procedures as EXAMPLE 2 above, 18.8 ml (200 mmol) of fluorobenzene and 0.31 g (2.3 mmol) of aluminum chloride were alkylated with 5.61 g (22.8 mmol) of (2,3-dichloropropyl)trichlorosilane for 10 min at 70° 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 fluorobenzene were distilled, the reaction products were vacuum distilled to give 3.39 g of [3,3-bis(fluorophenyl)propyl]trichlorosilane (bp; 121-122° C./0.5 torr, yield; 41%) as a mixutre of isomers.

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 fluorobenzene were distilled
  5. distillationdistilled

Sources & evidence

ORD record
ord-1388c80601624ea082e75cff451879fa
Source dataset
uspto-grants-2000_02
Patent number
US06022987

Reaction notes

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