Sulfuric Acid → 5-Bromo-1,3-diethyl-2-iodobenzene

Temperatur

60 °C

To a stirred mixture of 4-bromo-2,6-diethylaniline (13.6 g, 0.06 mol) in distilled water (14 ml) is added concentrated sulphuric acid (14 ml), followed by brief heating to 60° C. for 1 hour until dissolution is complete. The mixture is allowed to cool to room temperature then further cooled to approximately 0° C. in an ice/salt bath. To this slurry is added an aqueous solution of sodium nitrite (4.1 g, 0.059 mol) in distilled water (20 ml) dropwise over 15 minutes, maintaining the temperature below 5° C., followed by additional stirring for 30 minutes. The reaction mixture is allowed to come to room temperature and then a solution of aqueous potassium iodide (29.8 g, 0.18 mol) in distilled water (30 ml) is added dropwise at room temperature. After the addition is complete the solution is briefly heated to 80° C. then allowed to cool to room temperature again. The reaction mixture is extracted with ethyl acetate (150 ml×3) and the organic phase is washed with 1M aqueous hydrochloric acid (75 ml) and aqueous sodium thiosulfate (2×75 ml). The organic phase is dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to give 4-bromo-2,6-diethyl-1-iodobenzene (19 g) as an orange liquid.

1. temperatureto cool to room temperature
2. temperaturethen further cooled to approximately 0° C. in an ice/salt bath
3. temperaturemaintaining the temperature below 5° C.
4. customto come to room temperature
5. additionAfter the addition
6. temperatureis briefly heated to 80° C.
7. temperatureto cool to room temperature again
8. extractionThe reaction mixture is extracted with ethyl acetate (150 ml×3)
9. washthe organic phase is washed with 1M aqueous hydrochloric acid (75 ml) and aqueous sodium thiosulfate (2×75 ml)
10. dry with materialThe organic phase is dried over anhydrous sodium sulphate
11. concentrationconcentrated under reduced pressure
12. customThe residue is purified by column chromatography on silica gel

ORD-Eintrag

ord-37382491f9124fd38d3e0f5b482ad424

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08895761B2