1-Chloro-2,3-difluorobenzene → 2-(4-Chloro-2,3-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1907107Notizen

Reaktionsgleichung

C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[F:14].C(O[B:19]1[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]1)(C)C>C1COCC1.O.C(OCC)(=O)C>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([B:19]2[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]2)=[C:9]([F:13])[C:8]=1[F:14]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

A 2.5 M solution of n-butyllithium (2.69 ml, 6.73 mmol) in hexanes was added dropwise to a solution of 1-chloro-2,3-difluorobenzene (1 g, 6.73 mmol) in THF (25 mL) cooled to −78° C. After 45 minutes at −78° C., 2-isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (1.253 g, 6.73 mmol) was added dropwise after which the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was diluted with water and ethyl acetate and the organic phase was extracted twice with water. The aqueous extracts were combined and acidified with 12N HCl to pH 3. The product was then extracted with ethyl acetate. The organic phase was dried and concentrated under vacuum to yield the title compound as an oil product (0.93 g, 50% yield): 1H NMR (CDCl3): δ 7.42 (m, 1H), 7.17 (m, 1H), 1.37 (s, 12H).

Aufarbeitung

temperatureto warm to ambient temperature
extractionthe organic phase was extracted twice with water
extractionThe product was then extracted with ethyl acetate
customThe organic phase was dried
concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-d1a37b71a41c436e8dced213334c8539
Quelldatensatz: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08598085B2

Notizen zur Reaktion

Wird geladen…