Borane;tetrahydrofuran → 5-Iodo-2-nitrobenzaldehyde

To a solution of 5-iodo-2-nitrobenzoic acid (37 g, 126 mmol) (APIN) in anhydrous tetrahydrofuran (200 mL) at 0° C. was added borane tetrahydrofuran (1 M, 360 mL, 360 mmol) dropwise. The reaction mixture was then stirred at room temperature for 24 h. The mixture was concentrated and residue was partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over MgSO4, concentrated, and triturated. The precipitate 5-Iodo-2-nitro-phenyl)-methanol was collected as a yellow solid (20 g, 57%). The solid (5.5 g) was dissolved into dichloromethane (100 mL), and activated MnO2 (15 g) was added. The mixture was then heated at reflux for 4 h, cooled to room temperature, and filtered through a short pad of celite. The filtrated was concentrated to give 5-Iodo-2-nitro-benzaldehyde as a yellow solid (Yield 4.2 g, 76%).

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. customtriturated
8. customThe precipitate 5-Iodo-2-nitro-phenyl)-methanol was collected as a yellow solid (20 g, 57%)
9. dissolutionThe solid (5.5 g) was dissolved into dichloromethane (100 mL), and activated MnO2 (15 g)
10. additionwas added
11. temperatureThe mixture was then heated
12. temperatureat reflux for 4 h
13. temperaturecooled to room temperature
14. filtrationfiltered through a short pad of celite
15. concentrationThe filtrated was concentrated

ORD record

ord-f0a8736971db454eaf7afce49ae4d98f

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07495007B2