1-(Methylsulfinyl)dodecane

• 2-Bromobenzyl Alcohol [B1294]
• 1-(Methylsulfinyl)dodecane [D4044]
• Oxalyl Chloride [O0082]
• Triethylamine [T0424]
• Dichloromethane

A suspension of 1-(methylsulfinyl)dodecane (3.82 g, 16.3 mmol) in dry dichloromethane (84 mL) was cooled to –60 °C. To this solution, a suspension of oxalyl chloride (2.06 g, 16.3 mmol) in dry dichloromethane (16 mL) was then added dropwise, and the mixture was stirred at –60 °C for 15 min. Subsequently, a suspension of 2-bromobenzyl alcohol (2.00 g, 10.7 mmol) in dry dichloromethane (20 mL) was added dropwise and the reaction mixture was stirred at –60 °C for 30 min. Triethylamine (7.5 mL, 53.9 mmol) was added at the same temperature and the mixture was stirred further before allowing it to warm to room temperature. The reaction was quenched with water (100 mL), followed by addition of 2 mol/L HCl (100 mL) and the two layers were separated. The aqueous layer was extracted with dichloromethane (200 mL), and the combined organic layers were washed with brine (100 mL), dried over anhydrous Na₂SO₄, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (ethyl acetate:hexane = 1:99 - 5:95) to afford 2-bromobenzaldehyde as a colorless oil (1.39 g, 70% yield).

The reaction mixture was monitored by UPLC.
This reaction was carried out in a fume hood because CO and CO₂ were generated as byproducts.

2-Bromobenzaldehyde

¹H NMR (400 MHz, CDCl₃); δ 10.4 (s, 1H), 7.90 (m, 1H), 7.63 (m, 1H), 7.44 (m, 2H).

• New odorless protocols for the Swern and Corey–Kim oxidations
  • K. Nishide, S. Ohsugi, M. Fudesaka, S. Kodama, M. Node, Tetrahedron Lett. 2002, 43, 5177.