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 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 (15% EtOAc/Hex) to yield 5.0 g (58%) of the desired product Mp=64 66° C.; 1H NMR (DMSO) 7.37 (d, 2H, J=8.8 Hz), 6.93 (d, 2H, J=8.8 Hz), 4.68 (s, 2H), 4.24 (t, 2H, J=5.05 Hz), 3.93 (t, 2H, J=5.27 Hz); MS eI m/z 248 (M+).

1. washwashed with H2O (1×30 mL)
2. washNaHCO3 (2×25 mL), and brine ether (200 mL) and washed with H2O (1×30 mL)
3. extractionThe organic extract
4. dry with materialwas dried over MgSO4
5. concentrationconcentrated
6. customThe crude product was purified by silica gel chromatography (15% EtOAc/Hex)

ORD record

ord-29caadd00c3d4ee2b704ccfad01e8b32

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06326367B1