Hydrochloric Acid → 2-Bromo-4-iodophenol

Temperature

5 °C

Sodium iodide (14.2 g) and sodium hydroxide (3.8 g) were added to a solution of 2-bromophenol (XIX, 16.4 g) in methanol (250 mL). The resultant solution was chilled to 0° C. A commercial bleach solution (6% NaClO, 120 mL) was added drop wise at 0-3° C. over 2 h. After the addition, the reaction mixture was stirred for 1 h at 5° C., then treated with 10% sodium thiosulfate aqueous solution (100 mL) and acidified with concentrated HCl to pH 5-7. The mixture was extracted with EtOAc (150 mL×3). The combined organic layers were partitioned with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The resultant oil was purified by silica gel column chromatography; the product eluted with dichloromethane/hexane (2:3), to afford the desired product as a colorless solid (14.76 g, 52%).

1. additionAfter the addition
2. extractionThe mixture was extracted with EtOAc (150 mL×3)
3. customThe combined organic layers were partitioned with brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe resultant oil was purified by silica gel column chromatography
8. washthe product eluted with dichloromethane/hexane (2:3)

ORD record

ord-dcca15937dce4cb7a1265cf4a8e17c8b

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697720B2