Hydrochloric Acid → 2-TERT-BUTYL-4-IODOPHENOL

Temperature

0 °C

To a 250 mL round-bottom flask was added 2-tert-butylphenol (3.76 g, 25 mmol) in MeOH (50.0 ml) to give a colorless solution. Sodium hydroxide (1.200 g, 30.0 mmol) was added and the mix was stirred until the hydroxide was completely dissolved. The solution was cooled to 0° C. and treated with sodium iodide (1.75 g, 11.6 mmol) followed by dropwise addition of 10% sodium hypochlorite solution (7.2 ml, 11.6 mmol). The addition of sodium iodide followed by sodium hypochlorite was repeated twice and the mixture was stirred at 0° C. for 30 min. The mixture was treated with 10% w/w solution of sodium thiosulfate, stirred for 30 min and treated with concentrated HCl dropwise to a constant pH of 1. The mixture was extracted 3× with EtOAc. The extracts were combined, washed with brine, dried (MgSO4), filtered and concentrated. The crude oil was flash chromatographed on an ISCO 80 g silica cartridge eluting with hexane-->4:1 hexane/EtOAc to give a yellow oil (5.2 g, 75%).

1. customto give a colorless solution
2. dissolutionwas completely dissolved
3. stirringstirred for 30 min
4. extractionThe mixture was extracted 3× with EtOAc
5. washwashed with brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customchromatographed on an ISCO 80 g silica cartridge
10. washeluting with hexane

ORD record

ord-8c354b37d6e34d9987efd0da94cc36b7

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188104B2