Bromine → 5-Bromo-3-methylthiophene-2-carbaldehyde

Temperature

70 °C

To 0° C. cooled solution of 3-methylthiophene-2-carbaldehyde (10.0 g, 79.3 mmol, 1.0 eq) in DCM (100 mL) was added drop wise a solution of bromine (12.6 g, 79.3 mmol, 1.0 eq) and the resulting mixture was stirred 70° C. for 4 h. The reaction was cooled to room temperature and diluted with DCM (100 mL). The resulting organic layer was washed with water (100 mL), saturated sodium bicarbonate solution (100 mL), brine (100 mL), dried (Na2SO4) and filtered. The filtrate was rotary evaporated to afford 11 g of the desired product as a brown solid. 1HNMR (400 MHz, CDCl3) δ 9.87 (s, 1H), 6.93 (s, 1H), 2.51 (s, 3H); ESI-MS (m/z) 205, 207 [(MH)+, Br79,81].

1. temperatureThe reaction was cooled to room temperature
2. washThe resulting organic layer was washed with water (100 mL), saturated sodium bicarbonate solution (100 mL), brine (100 mL)
3. dry with materialdried (Na2SO4)
4. filtrationfiltered
5. customThe filtrate was rotary evaporated

ORD record

ord-fd38e8fb18814a2ca9369b495dbdae1a

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169242B2