1,2-Dibromoethane → 1-(2-Bromoethoxy)-4-methanesulfonylbenzene

Temperature

100 °C

To a solution of 4-(methylsulfonyl)phenol (0.30 g, 1.74 mmol) in MeCN (5 mL) was added Cs2CO3 (0.71 g, 2.18 mmol) and 1,2-dibromoethane (1.64 g, 8.71 mmol). The resulting mixture was heated in a sealed tube at 100° C. After 1.5 h, additional Cs2CO3 (0.4 g, 1.21 mmol) was added and heated at 100° C. for another 2 h. Upon cooling, the mixture was partitioned between EtOAc and 1N NaOH. The organic phase was washed with sat'd brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (0-70% EtOAc-hexanes gradient) to afford the title compound as a white solid (0.255 g, 53% yield): MS (ES) m/z 279 and 281 (M+1 Br isotopes).

1. temperatureheated at 100° C. for another 2 h
2. temperatureUpon cooling
3. customthe mixture was partitioned between EtOAc and 1N NaOH
4. washThe organic phase was washed with sat'd brine
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated in vacuo
7. customThe residue was purified by flash chromatography (0-70% EtOAc-hexanes gradient)

ORD record

ord-baab7953a8ad4ad6b8e53a3ce61364a7

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673948B2