Iodine → HCID 86726415, compound

Temperature

-78 °C

nBuLi (5.67 mL, 14.2 mmol) was added to a solution of tert-butyl (2,5-difluorophenyl)carbamate (1.08 g, 4.73 mmol) and TMEDA (2.14 mL, 14.2 mmol) in THF (21.6 mL) at −78° C. over 20 minutes, ensuring the internal temperature remained below −70° C. The resulting solution was stirred at −78° C. for 1 h. Iodine (3.60 g, 14.2 mmol) in THF (10 mL) was added dropwise over 30 min, also ensuring the internal temperature remained below −70° C. The resulting reaction was stirred for 1 h at −78° C., The reaction was quenched at −78° C. with water and the reaction warmed to room temperature. 10% Sodium thiosulfate was added until the iodine color dissipated and the mixture was then extracted with ethyl acetate (3×50 mL). The combined organic fractions were dried (MgSO4), filtered and concentrated. The crude material was purified on silica gel, eluting 0-60% EtOAc in hexanes over 28 minutes to afford tert-butyl (3,6-difluoro-2-iodophenyl)carbamate (1.14 g, 3.20 mmol) as a white crystalline solid. MS (ESI): m/z=300.2 (M+H-[t-Bu]).

1. customremained below −70° C
2. customremained below −70° C
3. customThe resulting reaction
4. stirringwas stirred for 1 h at −78° C.
5. customThe reaction was quenched at −78° C. with water
6. temperaturethe reaction warmed to room temperature
7. addition10% Sodium thiosulfate was added until the iodine color
8. extractionthe mixture was then extracted with ethyl acetate (3×50 mL)
9. dry with materialThe combined organic fractions were dried (MgSO4)
10. filtrationfiltered
11. concentrationconcentrated
12. customThe crude material was purified on silica gel
13. washeluting 0-60% EtOAc in hexanes over 28 minutes

ORD record

ord-724bf22c3c5643ac89ccb9ab1d945fee

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315475B2