Benzaldehyde → HCID 49962591, compound

Participants

Reaction Conditions

Reaction Steps

2,4 dibromothiophene (3 g, 12.4 mmol) was dissolved in Et2O (50 mL) and cooled to −78° C. BuLi (1.6 M in hexanes)(8.1 mL, 13 mmol, 1.05 eg) was added dropwise over 20 min. then the yellow solution was stirred at −78° C. for 1 hour. Benzaldehyde (1.45 g, 13.64 mmol, 1.1 eg) dissolved in Et2O (15 mL) was added dropwise at a rate to maintain internal temperature <−70° C., then reaction mixture was allowed to warm slowly to 0° C. Quenched with Sat NH4Cl (50 mL) and phases partitioned. Organic fraction was washed with brine, dried, concentrated. Residue was chromatographed with 10% EtOAc/hexane to yield the title compound as a pale yellow solid.

Provenance & Evidence