(1,1'-Biphenyl)-4-carbonitrile → Hexachloroantimonate

HRID 2273503Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:11])[CH:10]=1)[C:5]([Cl:7])=[O:6].[C:12]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=1.[Sb:26]([Cl:31])([Cl:30])([Cl:29])([Cl:28])[Cl:27]>C(Cl)(Cl)Cl>[C:12]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:13]=[CH:14][C:15]([C:18]2[N:19]=[C:18]([C:15]3[CH:16]=[CH:17][C:12]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:13][CH:14]=3)[O+:6]=[C:5]([C:4]3[CH:3]=[C:2]([Br:1])[CH:10]=[C:9]([Br:11])[CH:8]=3)[N:19]=2)=[CH:16][CH:17]=1.[Cl:27][Sb-:26]([Cl:7])([Cl:31])([Cl:30])([Cl:29])[Cl:28]

Participants

Conditions

Temperature: 0 °C

Procedure

2.98 g of 3,5-dibromobenzoyl chloride and 3.58 g of 4-biphenylcarbonitrile were dissolved in 40 mL of chloroform. The obtained solution was cooled to 0° C., and 2.99 g of antimony pentachloride was added dropwise to the cooled solution. The obtained mixed liquid was stirred at room temperature for 10 minutes, and then, heated under reflux for 14 hours. The obtained reaction mixture was cooled to room temperature, and then distilled under a reduced pressure to remove chloroform to give 4,6-bis(4-biphenylyl)-2-(3,5-dibromophenyl)-1,3,5-oxadiazin-1-ium=hexachloroantimonate as a red solid.

Workup

additionThe obtained mixed liquid
temperatureheated
temperatureunder reflux for 14 hours
customThe obtained reaction mixture
temperaturewas cooled to room temperature
distillationdistilled under a reduced pressure
customto remove chloroform

Sources & evidence

ORD record: ord-ba1c038a8b024af0ad4acf8aa9882bb3
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120773B2

Reaction notes

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