Ammonium Chloride → 2,3-Dibromothieno[2,3-c]pyridine

温度

-78 °C

To a cooled (−78° C.) solution of 3-bromo-thieno[2,3-c]pyridine (6.42 g, 30.0 mmol) in dry THF (150 mL) under nitrogen was added 2.0 M LDA (30.0 mL, 60.0 mmol) dropwise. The mixture was stirred at −78° C. for 1 h. A solution of NBS (10.7 g, 60 mmol) in THF (50 mL) was added to the reaction mixture dropwise keeping the temperature below −70° C. The mixture was then warmed to room temperature overnight. Saturated aqueous ammonium chloride (50 mL) was added to the mixture and layers were separated. The aqueous layer was extracted with EtOAc (2×60 mL). The combined organic fractions were washed with brine (50 mL), dried over sodium sulfate, and concentrated. Purification by column chromatography (100% DCM) afforded 4.5 g (55%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 7.62 (d, J=5.4

1. customthe temperature below −70° C
2. temperatureThe mixture was then warmed to room temperature overnight
3. customwere separated
4. extractionThe aqueous layer was extracted with EtOAc (2×60 mL)
5. washThe combined organic fractions were washed with brine (50 mL)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated
8. customPurification by column chromatography (100% DCM)

ORDレコード

ord-2dd8d6a0121c44ca977a0ff7100d66c3

出典データセット

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08378104B2