Methyl iodide → 3-Bromothioanisole

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 under nitrogen at room temperature and a solution of methyl iodide (4.51 g, 31.77 mmol) in 20 ml anhydrous methanol was then added. The reaction mixture was stirred overnight at room temperature, poured into 2 M aqueous NaOH solution (30 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 80° C. (0.3 mmHg) and isolated in 86.1% (4.62 g) yield. 1H NMR(CDCl3, 500 MHz) δ ppm: 2.44 (s, 3H, CH3), 7.1-7.4(m, 4H, Ar—H)GC-MS(relative intensity %): 202, 204(1:1, 100, M+), 187, 189(1:1, 11, 3-BrPhS+).

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 80° C. (0.3 mmHg)
7. customisolated in 86.1% (4.62 g)
8. customyield

ORD record

ord-455cc8f88e484053ab58a3c5919b47a3

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07459106B2