Dimethyl Sulfoxide → HCID 59470557, compound

To a 100 mL round bottom flask was added methyl 3,4,5-trihydroxybenzoate (7.00 g, 88.0 mmol) followed by 25 mL of dimethyl sulfoxide. Potassium Carbonate (7.88 g, 57.0 mmol), potassium iodide (31.6 mg, 0.19 mmol) and 1-bromo-2-fluoroethane (5.79 g, 45.6 mmol) were successively added followed by 25 mL more of dimethyl sulfoxide. The reaction mixture was stirred for 18 h after which it was diluted by adding water (100 mL). The mixture was poured into a separatory funnel and extracted with DCM (3×40 mL). The organic layer was then washed with water (4×120 mL) and brine, and dried over magnesium sulfate. The organic layer was then concentrated to obtain an oil. The crude oil was purified using silica gel flash chromatography (DCM/ether 39:1) to obtain 1.9 g (22%) of the title compound (Rf˜0.17 in 19:1 DCM/ether). 1H NMR (600 MHz, CDCl3): δ 7.25 (s, 2H), 5.96 (s, 2H), 4.7 (t of d, 2H, J=48, 1.2 Hz), 4.37 (t of d, 2H, J=24, 1.2 Hz), 3.87 (s, 3H). 13C NMR (150 MHz, CDCl3): δ 166.8, 149, 136.8, 126.4, 109.8, 82.16 (d, J=334 Hz), 72.6 (d, J=37.5), 52.3. MS (ESI): 231.4 (M+H, 100); FIRMS: Calc'd for C10H11FO5 (M+H): 231.06633; Found: 231.0664.

1. additionwas diluted
2. additionThe mixture was poured into a separatory funnel
3. extractionextracted with DCM (3×40 mL)
4. washThe organic layer was then washed with water (4×120 mL) and brine
5. dry with materialdried over magnesium sulfate
6. concentrationThe organic layer was then concentrated
7. customto obtain an oil
8. customThe crude oil was purified

ORD record

ord-4bf02e4d1f00455896ba4517561d405f

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08491868B2