4-Bromothiophene-2-carbaldehyde → HCID 57908828, compound

Participants

Reaction Steps

To a solution of 4-bromothiophene-2-carboxaldehyde (10.1 g, 52.8 mmol) in anhydrous THF (150 mL) at 0° C. under N2 was added dropwise 1.0 M LiHMDS (58 mL) in THF. After 30 min, a solution of 2.0 M benzylmagnesium chloride (27 mL) in THF was added dropwise. The resulting mixture was stirred at rt for 50 min. The reaction mixture was quenched with sat. NH4Cl and most of the THF was evaporated. The residue was diluted with ethyl acetate (150 mL), washed with water and brine, and dried over MgSO4. Purification by flash chromatography gave 1A as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ: 1.5 (s, broad, 2H), 2.8 (m, 1H), 3.08 (m, 1H), 4.4 (m, 1H), 6.8 (s, 1H), 7.1-7.3 (m, 6H).

Provenance & Evidence