Dimethyl Sulfide → HCID 59772401, compound

Temperature

65 °C

To a stirred solution of 2-(2-Bromo-benzyloxy)-5-chloro-benzonitrile Example 348A (1.52 g, 4.71 mmol) in DCE (50 mL) under argon was added BH3 DMS (30.0 mL, 18.8 mmol). The reaction mixture was heated at 65° C. for 14 h and then cooled to room temperature. The mixture was quenched with 1N HCl solution slowly (25 mL). This solution was then mixed with 1N NaOH solution (30 mL), and extracted with EtOAc (3×80 mL). The combined EtOAc extracts were washed with saturated NaHCO3 solution (1×40 mL) and brine (1×40 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give 0.92 g (60%) of crude 2-(2-Bromo-benzyloxy)-5-chloro-benzylamine Example 348B which was used as is without further purification. HPLC Rt=2.87 min (YMC S5 ODS column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm) LC/MS: M+H=326

1. temperaturecooled to room temperature
2. customThe mixture was quenched with 1N HCl solution slowly (25 mL)
3. additionThis solution was then mixed with 1N NaOH solution (30 mL)
4. extractionextracted with EtOAc (3×80 mL)
5. washThe combined EtOAc extracts were washed with saturated NaHCO3 solution (1×40 mL) and brine (1×40 mL)
6. dry with materialThe organic layer was dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-de831421b86341ccae5bd017d3ffeba7

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07417040B2