Reacción #1973971

Ecuación de reacción

sodium hypochlorite

hydroxide

sodium iodide

sodium iodide

sodium hypochlorite

HCl

Sodium hydroxide

sodium thiosulfate

2-tert-butylphenol

→

oil

Rendimiento 162.4%

2-tert-butyl-4-iodophenol

Rendimiento 162.4%

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto give a colorless solution
2. 2
   workup.DISSOLUTIONwas completely dissolved
3. 3
   workup.STIRRINGstirred for 30 min
4. 4
   ExtracciónThe mixture was extracted 3× with EtOAc
5. 5
   Lavadowashed with brine
6. 6
   Secadodried (MgSO4)
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated
9. 9
   Otrochromatographed on an ISCO 80 g silica cartridge
10. 10
    Lavadoeluting with hexane

Procedimiento

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%).

Fuente