Dimethyl Sulfide → HCID 58197886, compound

Participants

Reaction Steps

To a solution of TMEDA (32.2 g, 0.278 mol) in dry THF (150 mL) was added s-BuLi (1.3 M, 0.278 mol, 214 mL) at −78° C. The mixture was stirred at this temperature for 0.5 hour, and then a solution of 3,4-difluorobenzoic acid (20 g, 0.127 mol) in THF (100 mL) was added dropwise. After stirring for 1 hour, CuBr.DMS (3.9 g, 0.019 mol, 15% mol) was added, followed by 3-bromoprop-1-ene (46 g, 0.38 mol) in 50 mL of THF. The reaction mixture was allowed to warm to room temperature and was quenched with water. The aqueous layer was washed with Et2O, and acidified with 4 N HCl. The mixture was extracted with Et2O. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give 2-allyl-3,4-difluorobenzoic acid (22 g, 55%). 1H NMR (CDCl3): 3.91 (d, 2H), 5.06 (m, 2H), 6.01 (m, 1H), 7.12 (m, 1H), 7.90 (m, 1H).

Provenance & Evidence