Dimethylformamide → HCID 118307060, compound

To a mixture of 1-bromo-2-(but-3-en-1-yl)-4-fluorobenzene (0.5 g, 2.183 mmol) in tetrahydrofuran (10 mL) at −78° C. was added BuLi (1.048 mL, 2.62 mmol) dropwise. It was then stirred at this temperature for 1 h, then N,N-dimethylformamide (0.204 mL, 2.62 mmol) was added. The reaction mixture was stirred at −78° C. for 30 min, then warmed up to rt and stirred at rt for 1 h. It was then quenched with NH4Cl, extracted with ether. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by biotage, eluting with 10% EtOAc/hexane to obtain 2-(but-3-en-1-yl)-4-fluorobenzaldehyde (0.35 g, 90%) as an oil. 1H NMR (400 MHz, CDCl3) δ 10.22 (s, 1H), 7.88 (dd, J=8.6, 6.1 Hz, 1H), 7.08 (td, J=8.3, 2.6 Hz, 1H), 7.05-6.96 (m, 1H), 6.00-5.73 (m, 1H), 5.12-4.99 (m, 2H), 3.22-3.09 (m, 2H), 2.49-2.34 (m, 2H).

1. stirringThe reaction mixture was stirred at −78° C. for 30 min
2. stirringstirred at rt for 1 h
3. customIt was then quenched with NH4Cl
4. extractionextracted with ether
5. dry with materialThe organic layer was dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by biotage
9. washeluting with 10% EtOAc/hexane

ORD record

ord-06e5761b314a444caac238672d487730

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273067B2