Potassium Carbonate → 2-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzylsulfanyl]-benzofuran

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[S:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[OH:12])N=N1.Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([B:21]2[O:25][C:24]([CH3:27])([CH3:26])[C:23]([CH3:29])([CH3:28])[O:22]2)=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:26][C:24]1([CH3:27])[C:23]([CH3:28])([CH3:29])[O:22][B:21]([C:18]2[CH:17]=[CH:16][C:15]([CH2:14][S:1][C:5]3[O:12][C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=4[CH:4]=3)=[CH:20][CH:19]=2)[O:25]1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

Starting material 2-[1,2,3]Thiadiazol-4-yl-phenol was prepared according to literature procedure (M. A. Abramov, W. Dehaen, B. D'hooge, M. L. Petrov, S. Smeets, S. Toppet and M. Voets Tetrahedron, 2000, 56, 3933-3940). 2-[1,2,3]Thiadiazol-4-yl-phenol (241 mg, 1.35 mmol), 2-(4-Bromomethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (406 mg, 1.37 mmol, 1 eq), and K2CO3 (396 mg, 2.87 mmol, 1.9 eq) was mixed in 8 mL of CH3CN and heat to 90° C. under nitrogen atmosphere. After reaction was complete as monitored by TLC, the mixture was cooled to room temperature and solvent evaporated. The resulting crude material was subject to column chromatography (20% EtOAc in hexane) to give 2-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzylsulfanyl]-benzofuran (198 mg) in 40% yield. NMR: G8475-125. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.3 (s, 12 H) 4.1 (s, 2 H) 6.6 (d, J=1.0 Hz, 1 H) 7.2 (m, 4 H) 7.4 (d, J=7.8 Hz, 2 H) 7.7 (d, J=8.1 Hz, 2 H).

Aufarbeitung

customwas prepared
customAfter reaction
temperaturethe mixture was cooled to room temperature
customsolvent evaporated

Quellen und Nachweise

ORD-Eintrag: ord-4e1351bf5a37400b85f6b58ea4531508
Quelldatensatz: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07390833B2

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