Thionyl Chloride → 3,5-Dichloro-5H-dibenzo[a,d]cycloheptene

HRID 2290286Notes

Reaction equation

HRID 2290286 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7](O)[C:6]=2[CH:17]=1.S(Cl)([Cl:20])=O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7]([Cl:20])[C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 202322453-chloro-5H-dibenzo[a,d]cyclohepten-5-ol

Product 1

HCID 202261183,5-Dichloro-5H-dibenzo[a,d]cycloheptene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The thus dried 3-chloro-5H-dibenzo[a,d]cyclohepten-5-ol intermediate was mixed with 10 milliliters of benzene and 10 milliliters of thionyl chloride and the resulting mixture stirred at reflux temperature for 2 hours to obtain 3,5-dichloro-5H-dibenzo[a,d]cycloheptene intermediate in the reaction mixture. The mixture was cooled and evaporated under reduced pressure to recover the chloro intermediate as residue.

Workup

  1. temperatureat reflux temperature for 2 hours

Sources & evidence

ORD record
ord-59b8b8a2c772402798958b1c03bbbd8f
Source dataset
uspto-grants-1986_10
Patent number
US04616023

Reaction notes

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