Dimethylformamide → 2-Bromo-6-fluorobenzaldehyde

Temperature

0 °C

A solution of diisopropylamine (7.9 mL, 55 mmol) in anhydrous tetrahydrofuran (70 mL) cooled to 0° C. was treated dropwise with butyllithium (1.6 M in hexanes, 34.9 mL, 56 mmol). The mixture was stirred at 0° C. for 15 min, then it was cooled to −78° C., and 1-bromo-3-fluoro-benzene (6.1 mL, 56 mmol) was added over 10 min. The mixture was stirred at −78° C. for 1 h, then anhydrous N,N-dimethylformamide (4.9 mL, 64 mmol) was added dropwise over 5 min. The mixture was stirred for another 20 min, then acetic acid (8 mL) and water (180 mL) were added, warmed up to RT, and extracted with ethyl acetate (2×175 mL). The combined organic layers were washed with water (2×75 mL), brine (100 mL), dried over anhydrous sodium sulfate, and concentrated to yield the crude product which was purified by silica gel chromatography (20-30% EtOAc in hexanes) to give 2-bromo-6-fluorobenzaldehyde as a pale yellow solid. MS (ESI, pos. ion) m/z: 204 (M+1).

1. temperatureit was cooled to −78° C.
2. stirringThe mixture was stirred at −78° C. for 1 h
3. stirringThe mixture was stirred for another 20 min
4. temperaturewarmed up to RT
5. extractionextracted with ethyl acetate (2×175 mL)
6. washThe combined organic layers were washed with water (2×75 mL), brine (100 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated
9. customto yield the crude product which
10. customwas purified by silica gel chromatography (20-30% EtOAc in hexanes)

ORD record

ord-5ab88dc0304449e7b102c50a1613614f

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476297B2