Thionyl bromide → 1-(Bromomethyl)-4-(2-chloroethoxy)benzene

To 4-(2-chloroethoxy)benzylalcohol CAS No. [111728-87-1] (6.4 g, 34.31 mmol) in dioxane (100 mL) at 0° C. was added slowly thionylbromide (7.13 g, 34.31 mmol). The reaction was run at 0° C. after 5 min. The reaction mixture was diluted with ether (200 mL) and washed with H2O (1×30 mL) then NaHCO3 (2×25 mL), and brine (30 mL). The organic extract was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (15EtOAc/Hex) to yield 5.0 g (58%) of the desired product. MP=64–66° C.; 1H NMR (DMSO) 7.37 (d, 2 H, J=8.8 Hz), 6.93 (d, 2 H, J=8.8 Hz), 4.68 (s, 2 H), 4.24 (t, 2 H, J=5.05 Hz), 3.93 (t, 2 H, J=5.27 Hz); MS eI m/z 248 (M+).

1. washwashed with H2O (1×30 mL)
2. extractionThe organic extract
3. dry with materialwas dried over MgSO4
4. concentrationconcentrated
5. customThe crude product was purified by silica gel chromatography (15EtOAc/Hex)

ORD record

ord-a10f59470aa84b29b5e54d972a950490

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07041663B2