2-Bromo-5-methylsulfonylnitrobenzene → 4-(Methylsulfonyl)-2-nitro-1-vinylbenzene

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH:15](B1OC(C)(C)C(C)(C)O1)=[CH2:16]>>[CH3:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH:15]=[CH2:16])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1)(=[O:10])=[O:9]

Participants

Reactant 2

HCID 20603662-Bromo-5-methylsulfonylnitrobenzene

HCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 585219244-(Methylsulfonyl)-2-nitro-1-vinylbenzene

Procedure

Following the general method as outlined in Intermediate 20, starting from 2-bromo-5-methylsulfonylnitrobenzene and vinylboronic acid pinacol ester, the title compound was obtained as a brown oil in quantitative yield.

Sources & evidence

ORD record: ord-c5ca50a4fa81470985545ba9d3a26aac
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273769B2

Reaction notes

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