Ammonium Chloride → methyl 3-bromo-1H-pyrrole-2-carboxylate

Temperature

0 °C

Methyl 3-bromo-1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate (6.59 g, 19.15 mmol) was dissolved in 132 mL anhydrous methanol under nitrogen atmosphere and it was cooled at 0° C. Sodium methoxide (1.55 g, 28.69 mmol) was added and the reaction mixture was stirred at room temperature for 4 h. The reaction was poured into a saturated ammonium chloride solution and extracted twice with ethyl acetate. The organics were combined and washed with water, brine, dried over sodium sulphate, filtered and evaporated under reduced pressure. The crude was purified using SP1® Purification System (0% to 30%, hexane-ethyl acetate) to obtain 3.32 g (85% yield) of the title compound as a white solid.

1. extractionextracted twice with ethyl acetate
2. washwashed with water, brine
3. dry with materialdried over sodium sulphate
4. filtrationfiltered
5. customevaporated under reduced pressure
6. customThe crude was purified
7. customSP1® Purification System (0% to 30%, hexane-ethyl acetate)

ORD record

ord-d64183ba98ca41859c409bff60420a76

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388189B2