2-Bromo-5-methylsulfonylnitrobenzene → 1-Isopropenyl-4-(methylsulfonyl)-2-nitrobenzene

HRID 2390174Notes

Reaction equation

HRID 2390174 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/C)=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)(=[O:4])=[O:3].Br[C:18]1C=CC(S(C)(=O)=O)=CC=1[N+]([O-])=O.C(B1OC(C)(C)C(C)(C)O1)(C)=C>>[C:11]([C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][C:7]=1[N+:14]([O-:16])=[O:15])([CH3:12])=[CH2:18]

Participants

4

Reactant 3

HCID 20603662-Bromo-5-methylsulfonylnitrobenzeneHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 585219844-(methylsulfonyl)-2-nitro-1-[(1E)-prop-1-en-1-yl]benzene

Product 1

HCID 585218981-Isopropenyl-4-(methylsulfonyl)-2-nitrobenzene

Procedure

Following the general method as outlined in Intermediate 59, starting from 2-bromo-5-methylsulfonylnitrobenzene and isopropenylboronic acid pinacol ester, the title compound was obtained as a brown oil in quantitative yield after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-10c7eb26203042649ac57ecb2fead673
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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