Dimethyl Sulfide → Methyl 2-chloro-6-formyl-benzoate

Into a solution of methyl 2-chloro-6-vinylbenzoate (6.7 g, 34 mmol) in dry DCM (100 mL) was bubbled O3 at −78° C. over a 30 minute period. Next, nitrogen gas was bubbled into the solution until the solution was colorless. Dimethylsulfane (4.3 g, 68 mmol) was added dropwise and the resulting mixture was warmed to RT and stirred for 2 hours. The reaction mixture was subsequently washed with water (30 mL) and extracted with DCM (3×100 mL). The organic layers were combined, dried over Na2SO4, and concentrated. The crude product was purified by column chromatography eluting with a gradient of EtOAc (0-90%) and PE to give the title compound (3.8 g, 56%). 1H NMR (400 MHz, CDCl3) δ ppm 9.89 (s, 1H), 7.728 (d, J=7.2 Hz, 1H), 7.606 (d, J=8.0 Hz, 1H), 7.489 (t, J=8.0 Hz, 1H), 3.95 (s, 3H).

1. customNext, nitrogen gas was bubbled into the solution until the solution
2. washThe reaction mixture was subsequently washed with water (30 mL)
3. extractionextracted with DCM (3×100 mL)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. customThe crude product was purified by column chromatography
7. washeluting with a gradient of EtOAc (0-90%) and PE

ORD record

ord-d34b14f058a442219c9753484aec3eba

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09402841B2