METHYL BENZENESULFINATE synthesis
- Product Name:METHYL BENZENESULFINATE
- CAS Number:670-98-4
- Molecular formula:C7H8O2S
- Molecular Weight:156.2
Yield:670-98-4 80%
Reaction Conditions:
with N-Bromosuccinimide at 20;Inert atmosphere;
Steps:
Methyl benzenesulfinate1 (3e1)
To a solution of 1,2-diphenyldisulfane (0.08 mol, 17.5 g) in MeOH (200 mL) was slowly added NBS (0.12 mol, 21.2 g) at room temperature. The reaction mixture was stirred, and when the reaction was finished (followed by TLC), it was diluted with CH2Cl2 (200 mL), washed with a saturated solution of NaHSO3 (10 mL) and several times with a saturated solution of NaHCO3 (4 x 20 mL) The organic layer was dried over anhydrous Na2SO4 and the solvent removed under vacuum. Flash cromathography ( AcOEt-hexane, 1:6 ); yield: 80% ( 10 g ); yellow oil; 1H NMR (400 MHz, CDCl3) δ 7.81 - 7.58 (m, 2H), 7.58 - 7.35 (m, 3H), 3.42 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 143.88, 132.21, 129.06, 125.36, 49.56. HRMS (ESI): C7H8O2S Neutral mass: 156.02450, Observed neutral mass: 156.0239, Observed ([M+Na])+ : 179.0127.
References:
Ma, Long-jun;Li, Guang-xun;Huang, Jin;Zhu, Jin;Tang, Zhuo [Tetrahedron Letters,2018,vol. 59,# 16,p. 1600 - 1603] Location in patent:supporting information
