Water → 5,6-Bis(4-bromophenyl)-2,2'-bipyridine

HRID 1502563Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)N=N[C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[CH:27]12CC(C=C1)C=[CH:28]2.C1(C)C(C)=CC=CC=1.O>C1(C)C=CC=CC=1>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[CH:27]=[CH:28][C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[N:9][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 140 °C

Procedure

In a 500 mL three-neck flask were put 13 g (27 mmol) of 5,6-bis(4-bromophenyl)-3-(2-pyridyl)-1,2,4-triazine, 9.0 mL (83 mmol) of 2,5-Norbornadiene, and 150 mL of xylene. This mixture was refluxed at 140° C. for 5 hours under a nitrogen stream. After a certain time, water was added to the mixture, and an aqueous layer was extracted with toluene. The extract was washed with a saturated saline together with the organic layer, and the organic layer was then dried with magnesium sulfate. The mixture was subjected to gravity filtration, and the obtained filtrate was concentrated to give a solid. The solid was refined with silica gel column chromatography (toluene), so that a target substance, 7.5 g of light-yellow powder was obtained in a yield of 59%.

Workup

customIn a 500 mL three-neck flask were put
extractionan aqueous layer was extracted with toluene
washThe extract was washed with a saturated saline together with the organic layer
dry with materialthe organic layer was then dried with magnesium sulfate
filtrationThe mixture was subjected to gravity filtration
concentrationthe obtained filtrate was concentrated
customto give a solid

Sources & evidence

ORD record: ord-b62f033a0c094bbeaaf3c9f1834392e0
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09209408B2

Reaction notes

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