Sulfuric Acid → 3-iodo-5-(trifluoroMethyl)phenol

Temperature

0 °C

To a stirred solution of 3-amino-5-(trifluoromethyl)phenol (42 g, 237.12 mmol, 1.00 equiv) in water (80 mL) at 0° C. was added 50% sulfuric acid (240 mL) dropwise. The resulting solution was stirred at 0° C. for 30 min. A solution of sodium nitrite (24.5 g, 355.07 mmol, 1.50 equiv) in water (90 mL) followed by a solution of potassium iodide (78.7 g) in water (80 mL) was added dropwise at 0° C. The resulting solution was stirred at 25° C. for 8 h. The reaction mixture was extracted with 2×100 mL of ethyl acetate. The combined organic layers were washed with 2×150 mL of saturated Na2SO3 solution and 2×200 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrate under reduced pressure. The residue was purified on a silica gel column eluted with 0-7% of ethyl acetate in petroleum ether to give 54 g (79%) of 3-iodo-5-(trifluoromethyl)phenol as a yellow oil.

1. additionwas added dropwise at 0° C
2. stirringThe resulting solution was stirred at 25° C. for 8 h
3. extractionThe reaction mixture was extracted with 2×100 mL of ethyl acetate
4. washThe combined organic layers were washed with 2×150 mL of saturated Na2SO3 solution and 2×200 mL of brine
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
6. concentrationconcentrate under reduced pressure
7. customThe residue was purified on a silica gel column
8. washeluted with 0-7% of ethyl acetate in petroleum ether

ORD record

ord-cfe75ccd77ce46aea135fd2c9e1da67b

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952026B2