Reacción #2460313

Ecuación de reacción

NaOH

3-bromobenzenethiol

sodium methoxide

benzyl bromide

→

3-bromophenyl benzyl sulfide

Disolventes

methanol

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe reaction mixture was stirred overnight at room temperature
2. 2
   Extracciónextracted three times with ether (60 ml×3)
3. 3
   LavadoThe combined organic layer was washed with saturated sodium chloride solution
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   OtroAfter removal of solvent
6. 6
   workup.DISTILLATIONthe product was purified by distillation at 161° C.
7. 7
   Otro0.3 mmHg and isolated in 85.5% (6.31 g)
8. 8
   Otroyield

Procedimiento

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+).

Fuente