Sodium hydride → HCID 18978687, compound

Participants

Reaction Steps

To a suspension of 2,4-dibromo-N-(4-(trifluoromethyl)benzyl)butanamide (6.8 g, 16.9 mmol) in tetrahydrofuran (200 mL) was added NaH (1.35 g, 34 mmol) and the reaction was stirred at rt for 4 h. The reaction mixture was then diluted with water and twice extracted with 30 mL of ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and evaporated to dryness. The residue was purified by silica gel chromatography eluting with 0-40% ethyl acetate/hexanes to afford 2.8 g of 3-bromo-1-(4-(trifluoromethyl)benzyl)pyrrolidin-2-one (48%). LCMS (method Q) RT 0.90 min, m/z 322.1 (M+H+; 1H NMR (400 MHz, chloroform-d) δ 12.39 (d, J=8.0 Hz, 2H), 12.16 (d, J=8.0 Hz, 2H), 9.46-9.38 (m, 1H), 9.25 (d, J=1.8 Hz, 2H), 8.27-8.17 (m, 1H), 7.99 (s, 1H), 7.43-7.31 (m, 1H), 7.14-7.05 (m, 1H).

Provenance & Evidence