Methanol → Methyl 4-bromo-1H-pyrrole-2-carboxylate

To a solution of Example 1B (20 g, 68 mmol) in methanol (100 mL), a solution of NaOMe (1M in MeOH, 34 mL, 34 mmol) was added slowly. This mixture was then stirred at ambient temperature for 1 h after which it was diluted with water (300 mL) and the organic layer was separated. The aqueous phase was extracted with CH2Cl2 and the combined organic layer and extracts were washed with water (2×50 mL), dried (MgSO4) and evaporated under reduced pressure. Recrystallization of the residue from hexane gave 4-Bromo-2-methoxycarbonylpyrrole (Example 1C, 12 g, 85%) as a white solid. LC-MS, [M−H]+=203. 1H NMR (DMSO-d6, 400 MHz): δ 12.31 (brs, 1H), 7.16 (s, 1H), 6.81 (s, 1H), 3.75 (s, 3H).

1. customthe organic layer was separated
2. extractionThe aqueous phase was extracted with CH2Cl2
3. washthe combined organic layer and extracts were washed with water (2×50 mL)
4. dry with materialdried (MgSO4)
5. customevaporated under reduced pressure
6. customRecrystallization of the residue from hexane

ORD 기록

ord-38f16d2f412f41de92f11abaf517e1fd

출처 데이터셋

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08754211B2