Tetrahydrofuran → 3-Bromo-4-hexylthiophene

Compound 51 (70 g, 0.173 mol) was mixed with dry THF (400 mL). To this mixture, n-butyllithium (138 mL, 2.5M in hexane, 0.345 mol) was added dropwise at −78° C. under argon. The resulting mixture was stirred for 10 minutes, then water (30 mL) was added to quench the reaction. The THF was evaporated and the organic was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (2×100 mL), water (70 mL) and dried over MgSO4. After evaporation of the solvent, the resulting crude product was purified by vacuum distillation (72-74° C. at 0.17 mbar) to yield 52 (35.3 g, 82.6% yield). GC/MS: 246 g/mol (M-1). 1H NMR (CD2Cl2): δ 7.22 (s, 1H), 6.96 (s, 1H), 2.57 (t, 2H), 1.61 (m, 2H), 1.32 (m, 6H), 0.88 (t, 3H). 13C NMR: 141.92, 122.87, 120.95, 112.89, 31.88, 30.07, 29.53, 29.20, 22.88, 14.14.

1. customto quench
2. customthe reaction
3. customThe THF was evaporated
4. extractionthe organic was extracted with ethyl acetate (2×100 mL)
5. washThe combined organic layers were washed with brine (2×100 mL), water (70 mL)
6. dry with materialdried over MgSO4
7. customAfter evaporation of the solvent
8. distillationthe resulting crude product was purified by vacuum distillation (72-74° C. at 0.17 mbar)

ORD record

ord-e51de1e35de04171adc9f687a0615a3f

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389669B2