Nitric Acid → HCID 68285413, compound

Temperature

-5 °C

Sulfuric acid (27.6 g, 15.0 ml, 281.0 mmol) was added in a dropwise manner to ethyl 3,5-dibromothiophene-2-carboxylate (Prepared according to procedure reported in JCS Perkin Trans-1: Organic and Bioorganic Chemistry (1972-1999), 1973, p 1766-1770), 5.0 g (15.92 mmol), at room temperature (about 25° C.). The reaction mixture was then cooled to −5° C. and to the cooled mixture was added nitric acid (2.0 g, 2.04 ml, 31.84 mmol) slowly. The reaction mixture was then stirred at 0° C. for 1 hr. The progress of the reaction was monitored by TLC. The reaction mixture was then poured onto ice-water (150 ml). The mixture so obtained was extracted with ethyl acetate (2×100 ml). The combined organic layer was dried over sodium sulphate and was concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography over silica gel (100-200 mesh) using 2% ethyl acetate in hexanes as an eluent to obtain the title compound (3.40 g, 59.54%).

1. additionThe reaction mixture was then poured onto ice-water (150 ml)
2. customThe mixture so obtained
3. extractionwas extracted with ethyl acetate (2×100 ml)
4. dry with materialThe combined organic layer was dried over sodium sulphate
5. concentrationwas concentrated under reduced pressure
6. customto obtain a crude product, which
7. customwas then purified by column chromatography over silica gel (100-200 mesh)

ORD record

ord-4430c0c2806b4b48ae515913b494ff88

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09072731B2