1,2-Dichloroethane → 5-Chloro-2-iodobenzaldehyde

To a solution of 5-chloro-2-iodo benzoic acid (4.92 g, 17 mmol) (TRANS) in anhydrous tetrahydrofuran (100 mL) at 0° C. was added borane tetrahydrofuran (1 M, 34 mL, 34 mmol) dropwise. The reaction mixture was then stirred at room temperature for 18 h. The mixture was concentrated and residue was partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over MgSO4, and concentrated to give a colorless oil. The oil was dissolved into 1,2-dichloroethane (50 mL), and activated MnO2 (15 g) was added. The mixture was then heated at reflux for 2 h, cooled to room temperature, and filtered through a short pad of celite. The filtrated was concentrated and purified by chromatography (EtOAc:hexanes=1;8) to give 5-chloro-2-Iodo-benzaldehyde as a white solid (Yield 5.5 g, 25%).

1. concentrationThe mixture was concentrated
2. customresidue was partitioned between ethyl acetate and water
3. customOrganic layer was separated
4. washwashed with brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. customto give a colorless oil
8. additionwas added
9. temperatureThe mixture was then heated
10. temperatureat reflux for 2 h
11. temperaturecooled to room temperature
12. filtrationfiltered through a short pad of celite
13. concentrationThe filtrated was concentrated
14. custompurified by chromatography (EtOAc:hexanes=1;8)

ORD record

ord-e3e0f6e74898478bb0b8ad6c025148a1

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07495007B2