4-Iodobenzoic acid → 4-Iodobenzaldehyde

To a suspension of 4-iodobenzoic acid (14.88 g) in dry tetrahydrofuran (75 ml) was added borane dimethyl sulphide (6.12 ml ) dropwise under a nitrogen atmosphere. The reaction mixture was heated under reflux for 1 hr, after which time the reaction mixture was cooled to room temperature and evaporated under reduced pressure. The residue was dissolved indichloromethane (20 ml) and added to a suspension of the pyridinium chlorochromate (14.23 g) in dichloromethane (100 ml). The resulting mixture was heated under reflux for 1 hr and allowed to cool to room temperature. The resulting mixture was diluted with diethyl ether (250 ml) and filtered through a plug of arbocel. The filtrate was evaporated under reduced pressure, and the crude product was purified by column chromatography over silica gel eluting with dichloromethane to afford the title compound as a white solid (11.33 g).

1. temperatureThe reaction mixture was heated
2. temperatureunder reflux for 1 hr
3. customevaporated under reduced pressure
4. dissolutionThe residue was dissolved indichloromethane (20 ml)
5. additionadded to a suspension of the pyridinium chlorochromate (14.23 g) in dichloromethane (100 ml)
6. temperatureThe resulting mixture was heated
7. temperatureunder reflux for 1 hr
8. temperatureto cool to room temperature
9. additionThe resulting mixture was diluted with diethyl ether (250 ml)
10. filtrationfiltered through a plug of arbocel
11. customThe filtrate was evaporated under reduced pressure
12. customthe crude product was purified by column chromatography over silica gel eluting with dichloromethane

ORD record

ord-ee96540317304ae683786b606ece91d6

Source dataset

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06200978B1