Benzyl Bromide → HCID 264185, compound

3-bromobenzenethiol (5 g, 26.44 mmol) was added to a solution of sodium methoxide (1.43 g, 26.48 mmol) in 20 ml of anhydrous methanol. The mixture was stirred for 30 min at room temperature and a solution of benzyl bromide (4.53 g, 26.48 mmol) in 20 ml anhydrous methanol was then added. The reaction mixture was stirred overnight at room temperature, poured into 2M o aqueous NaOH solution (40 ml) and extracted three times with ether (60 ml×3). The combined organic layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After removal of solvent, the product was purified by distillation at 161° C., 0.3 mmHg and isolated in 85.5% (6.31 g) yield. 1H NMR (CDCl3, 500 MHz) δ ppm: 4.12 (s, 2H, CH2), 7.0-7.5 (m, 4H, Ar—H)GC-MS (relative intensity %): 278, 280 (1:1, 30.8, M+), 91(100, PhCH2+).

1. stirringThe reaction mixture was stirred overnight at room temperature
2. extractionextracted three times with ether (60 ml×3)
3. washThe combined organic layer was washed with saturated sodium chloride solution
4. dry with materialdried over anhydrous magnesium sulfate
5. customAfter removal of solvent
6. distillationthe product was purified by distillation at 161° C.
7. custom0.3 mmHg and isolated in 85.5% (6.31 g)
8. customyield

ORD record

ord-fa2539ae0aa144ffbfe16bb40fbc5444

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07459106B2