Water → 2-Bromo-3-decanyldithieno[3,2-b:2',3'-d]thiophene

3-decanyldithieno[3,2-b:2′,3′-d]thiophene (91) (9.03 g, 0.027 mol) was dissolved in DMF (100 mL). To this solution, N-bromosuccinimide (NBS) (4.78 g, 0.027 mol) in DMF (50 mL) was added dropwise in the dark under argon. The resulting mixture was stirred at 0° C. for three hours. GC/MS showed a single peak at 415. This solution was poured into water (500 mL). Organic solution was extracted with hexane (3×100 mL). The combined organic solutions were washed with brine (2×50 mL) and water (50 mL). After drying over MgSO4, the hexane was evaporated. The crude product was purified by column chromatography and eluted with hexane to yield the target compound (10.1 g, 90.2%). 1HNMR: solvent, CD2Cl2. δ 7.39 (d, 1H), 7.29 (d, 1H), 2.74 (t, 2H), 1.74-1.33 (m, 16H), 0.89 (t, 3H). 13CNMR: 140.89, 140.63, 136.00, 131.55, 129.22, 126.58, 121.04, 108.89, 32.31, 29.94, 29.73 (overlap), 29.35, 28.49, 23.09, 14.27.

1. extractionOrganic solution was extracted with hexane (3×100 mL)
2. washThe combined organic solutions were washed with brine (2×50 mL) and water (50 mL)
3. dry with materialAfter drying over MgSO4
4. customthe hexane was evaporated
5. customThe crude product was purified by column chromatography
6. washeluted with hexane

ORD record

ord-d58c29f9bfce43c880989c17410631c2

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08349998B2