Benzaldehyde → HCID 49962591, compound

Temperature

-78 °C

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.

1. additionwas added dropwise at a rate
2. temperatureto maintain internal temperature <−70° C.
3. customreaction mixture
4. temperatureto warm slowly to 0° C
5. customQuenched with Sat NH4Cl (50 mL) and phases
6. custompartitioned
7. washOrganic fraction was washed with brine
8. customdried
9. concentrationconcentrated
10. customResidue was chromatographed with 10% EtOAc/hexane

ORD record

ord-5c069f0fe1c64f93b94ea4c33f8aa42b

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07279478B2