Dimethylformamide → Methyl 2-(5-tert-butyl-2-hydroxy-4-nitrophenyl)-2-methylpropanoate

HRID 76780

Reaktionsgleichung

Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=1[OH:15].[CH3:16]/[C:17](/[CH3:26])=[C:18](/[O:24][CH3:25])\[O:19][Si](C)(C)C.CN(C)C=O>O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.[F-].[Zn+2].[F-]>[C:8]([C:6]1[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]([OH:15])=[C:2]([C:17]([CH3:26])([CH3:16])[C:18]([O:24][CH3:25])=[O:19])[CH:7]=1)([CH3:11])([CH3:10])[CH3:9]

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

A mixture of 2-bromo-4-tert-butyl-5-nitrophenol (15.00 g, 54.72 mmol), bis(tri-tert-butylphosphine)palladium(0) (1.422 g, 2.783 mmol), zinc fluoride (2.82 g, 27.27 mmol), methyl trimethylsilyl dimethylketene acetal (MTDA) (19.35 g, 111.0 mmol), and dimethylformamide (150 mL) was heated at 70° C. for 18 h. The mixture was cooled to room temperature and diluted with water. After stirring for one hour, the aqueous phase was extracted with MTBE. The organic layer was dried in vacuo to afford the crude product as a brown solid. Purification of the product was accomplished by trituration in n-heptane. 1H-NMR (400 MHZ, DMSO-d6) δ 10.38 (s, 1H); 7.37 (s, 1H); 6.79 (s, 1H); 3.54 (s, 3H); 1.45 (s, 6H); 1.32 (s, 9H)

Aufarbeitung

temperatureThe mixture was cooled to room temperature
extractionthe aqueous phase was extracted with MTBE
customThe organic layer was dried in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-b7df57c9d10c4480a2c699a7d163b300
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08835639B2

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