Boron trifluoride → Chloride

HRID 2072300Notes

Reaction equation

HRID 2072300 reaction equation
[CH2:1](SC1C=C(C=C[C:16]=1[C:17]([Cl:19])=O)C=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-:20].[Cl-].[Cl-].[Al+3].B(F)(F)F.[N+:28](C)([O-:30])=[O:29]>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[N+:28]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([O-:30])=[O:29].[N+:28]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])([O-:30])=[O:29].[Cl-:19].[Cl:20][CH:17]([Cl:19])[CH3:16]

Participants

10

Reactant 4

HCID 6356Boron trifluorideHCID 6375NitromethaneHCID 6451240Aluminum(III) ChlorideHCID 536823133-Benzylmercapto-4-chlorocarbonyl benzaldehyde

Product 4

HCID 312ChlorideHCID 63651,1-DichloroethaneHCID 69442-NitrotolueneHCID 7416Nitrobenzene

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

The compound of formula (a), 3-benzylmercapto-4-chlorocarbonyl benzaldehyde, prepared according to the procedure set forth in the Preparation below, is cyclized with a Lewis acid, e.g., aluminum trichloride, stannic chloride, boron trifluoride, and the like, in the presence of an inert organic solvent, e.g., nitromethane, nitrobenzene, nitrotoluene, methylene, chloride, chloroform, carbon tetrachloride, dichloroethane, and the like, or mixtures thereof, at a temperature of from about 0° to about 40° C, for from about 5 minutes to about 3 hours, preferably from about 15° to about 20° C, for from about 10 minutes to about 2 hours, to obtain the novel non-pharmaceutical intermediate compound of formula (1), 6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-carboxaldehyde.

Workup

  1. customset forth in the Preparation below,

Sources & evidence

ORD record
ord-16fcecf66fa649a49a7f6379da959a23
Source dataset
uspto-grants-1977_09
Patent number
US04051148

Reaction notes

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