Water → 2-Bromo-4,5,6,7-tetrahydro-1-benzothiophen-4-one

In a 500 mL round bottomed flask was placed 6,7-dihydro-4-benzo[b]thiophenone (8.3 g, 54 mmol) and then dissolved in acetic acid (30 mL). To the mixture was added water (30 mL) and the solution was stirred for 30 min at rt. To the mixture was dropwise added freshly prepared solution of bromine (9.4 g, 59 mmol) in acetic acid (50 mL) over 10 min. After addition of the Br2, the mixture was stirred for 1.5 h at the same temperature. The mixture was concentrated under reduced pressure and the residue was diluted with ether (150 mL), which was washed with 1N NaOH aq (100 mL). The aqueous phase was extracted with ether (100 mL) and the combined organic phase was washed with brine (100 mL), dried over anhydrous MgSO4 and then decolorized with activated carbon. Insoluble materials were removed by filtration through Celite pad and the filtrate was concentrated under reduced pressure. The residue was suspended in 50 mL of MeOH and then stirred for 15 min for washing. The precipitate was collected by filtration to obtain the title compound (5.65 g; 45%) as a yellowish crystalline solid. From the mother liquid, 2nd crop of the title compound (6.66 g; 53%) has been obtained. LCMS: (FA) ES+ 231, 233. 1H NMR (300 MHz, d1-chloroform) δ: 7.35 (s, 1H), 2.95 (t, 2H), 2.52-2.56 (m, 2H), 2.17-2.25 (m, 2H).

1. customIn a 500 mL round bottomed flask was placed
2. stirringthe mixture was stirred for 1.5 h at the same temperature
3. concentrationThe mixture was concentrated under reduced pressure
4. additionthe residue was diluted with ether (150 mL), which
5. washwas washed with 1N NaOH aq (100 mL)
6. extractionThe aqueous phase was extracted with ether (100 mL)
7. washthe combined organic phase was washed with brine (100 mL)
8. dry with materialdried over anhydrous MgSO4
9. customInsoluble materials were removed by filtration through Celite pad
10. concentrationthe filtrate was concentrated under reduced pressure
11. stirringstirred for 15 min
12. washfor washing
13. filtrationThe precipitate was collected by filtration

ORDレコード

ord-02626d67f2b14db8a261216df86c36dc

出典データセット

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08765746B2