Ethyl Acetate → 1-Ethyl-4-methylsulfonyl-2-nitrobenzene

HRID 518506Notes

Reaction equation

HRID 518506 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].[CH2:15](B(O)O)[CH3:16].C([O-])([O-])=O.[K+].[K+].CC(=O)OCC>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:15]([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])[CH3:16]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 521157Ethylboronic acidHCID 20603662-Bromo-5-methylsulfonylnitrobenzene

Product 1

HCID 582661211-Ethyl-4-methylsulfonyl-2-nitrobenzeneYield 41.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

bromo-4-methylsulfonyl-2-nitrobenzene (2 g, 7.0 mmol), ethylboronic acid (0.57 g, 7.7 mmol), K2CO3 (3.0 g, 21 mmol), Pd(dppf)Cl2 (0.29 g, 0.35 mmol) in 1,4-dioxane/water (4:1) (24 mL) were heated at 85° C. under N2 overnight. Silica gel chromatography (PE:EA=6:1) gave the title compound (0.66 g, 40%) as a brown solid.

Sources & evidence

ORD record
ord-cc922a964cd14a84a4cf3e863805fc95
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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