Reaktion #2266624

Reaktionsgleichung

product

8-bromo-6-chloro-1,2,3,4-tetrahydrodibenzo[b,d]furan-2-ol

sodium benzenesulfinate

cesium carbonate

xantphos

→

6-chloro-8-(phenylsulfonyl)-1,2,3,4-tetrahydrodibenzo[b,d]furan-2-ol

Ausbeute 28.3%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction flask was purged with argon
2. 2
   TemperaturAfter cooling to ambient temperature
3. 3
   workup.ADDITIONthe reaction mixture was diluted with dichloromethane
4. 4
   Filtrationfiltered through a celite bed
5. 5
   EinengenThe filtrate was concentrated in vacuo
6. 6
   Sonstigethe residue purified by flash column chromatography (SiO2, 9:1 hexanes/ethyl acetate)
7. 7
   Sonstigetriturated with MTBE

Vorschrift

A mixture of the product of step B (120 mg, 0.39 mmol), sodium benzenesulfinate (77 mg, 0.47 mmol), di-palladium-tris(dibenzylideneacetone) (36 mg, 0.04 mmol), cesium carbonate (190 mg, 0.58 mmol) and xantphos (45 mg, 0.08 mmol) was suspended in anhydrous toluene (5.0 mL). The reaction flask was purged with argon and heated to 110° C. for 1 h. After cooling to ambient temperature, the reaction mixture was diluted with dichloromethane and filtered through a celite bed. The filtrate was concentrated in vacuo and the residue purified by flash column chromatography (SiO2, 9:1 hexanes/ethyl acetate) and triturated with MTBE to give 6-chloro-8-(phenylsulfonyl)-1,2,3,4-tetrahydrodibenzo[b,d]furan-2-ol (40 mg, 27%, AUC HPLC 97.1%) as a white solid: mp 236-240° C.; 1H NMR (DMSO-d6, 400 MHz) δ 8.15 (d, J=1.6 Hz, 1H), 8.05-8.01 (m, 2H), 7.89 (d, J=1.6 Hz, 1H), 7.71-7.66 (m, 1H), 7.64-7.59 (m, 2H), 4.92 (d, J=4.0 Hz, 1H), 4.11-4.04 (m, 1H), 2.94-2.76 (m, 3H), 2.60-2.52 (m, 1H), 2.00-1.87 (m, 2H); ESI MS m/z 363 [M+H]+.

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