Dimethyl Sulfide → HCID 77230674, compound

Temperature

120 °C

To a round bottom flask charged with a mixture of 5-bromo-7-chloro-2-benzofuran-1(3H)-one and 7-bromo-5-chloro-2-benzofuran-1(3H)-one (120 mg, 0.48 mmol) and a stir bar was added PdCl2(dppf)-DCM complex (40 mg, 0.048 mmol) allyl tri-n-butyltin (241 mg, 0.73 mmol), lithium chloride (41 mg, 0.97 mmol), and toluene (15 mL). The mixture was purged three times with nitrogen, and heated to 120° C. for 4 hours. LC showed formation of the desired product, which was purified by silica gel chromatography (Hexane-EtOAc). The resulting oil yellow oil was then dissolved in methanol (10 mL). The solution was cooled to −78° C. To this solution was bubbled ozone through until it turned light blue. Excess ozone was removed by bubbling nitrogen through the solution, which was followed by addition of dimethyl sulfide (0.21 mL, 2.9 mmol). The reaction was allowed to warm to RT slowly. LC showed formation of the desired product. The reaction was diluted with EtOAc (50 mL), washed with brine, dried over sodium sulfate, adsorbed onto silica gel, and purified by flash chromatography as a mixture of (7-chloro-1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde and (6-chloro-3-oxo-1,3-dihydro-2-benzofuran-4-yl)acetaldehyde. LC/MS: (IE, m/z) (M+1)+=211.1.

1. customThe mixture was purged three times with nitrogen
2. customwas purified by silica gel chromatography (Hexane-EtOAc)
3. dissolutionThe resulting oil yellow oil was then dissolved in methanol (10 mL)
4. temperatureThe solution was cooled to −78° C
5. customTo this solution was bubbled ozone through until it
6. customExcess ozone was removed
7. customby bubbling nitrogen through the solution, which
8. temperatureto warm to RT slowly

ORD record

ord-1ecae24cb6b7432aabbfc2fb20ca62d8

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056859B2