Water → 1369356-10-4

To a solution of 2-methylthiophene-3-carbaldehyde (0.204 g, 1.62 mmol, Comins, D. L.; Killpack, M. O. J. Org. Chem. 1987, 52(1), 104-109) in DMF (10 mL) was added N-bromosuccinimide (0.43 g, 2.43 mmol); the resulting mixture was stirred at rt for about 16 h and then water (75 mL) and diethyl ether (25 mL) were added. The layers were separated and the aqueous layer was extracted with diethyl ether (2×30 mL). The combined organic layers were washed with water (15 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, diethyl ether/hexanes 1:9) to give 5-bromo-2-methylthiophene-3-carbaldehyde (0.272 g, 1.33 mmol, 82%) as a yellow oil which crystallized on standing: 1H-NMR (CDCl3, Bruker 400 MHz) δ 2.72 (3 H, s), 7.33 (1 H, s), 9.9 (1 H, s).

1. customThe layers were separated
2. extractionthe aqueous layer was extracted with diethyl ether (2×30 mL)
3. washThe combined organic layers were washed with water (15 mL)
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by column chromatography (SiO2, diethyl ether/hexanes 1:9)

ORD record

ord-029f184e04e14ea0a4cb03c894674751

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150592B2