Iodopentafluoroethane → 1-Bromo-4-pentafluoroethylsulfanylbenzene

The title compound was prepared using perfluoroalkylation conditions originally described by Popov et. al. J. Fluorine Chem. 1982, 21, 365. To a solution of 4-bromobenzenethiol (500 mg, 2.64 mmol, 1.00 eq) and triethylbenzyl ammonium chloride (60 mg, 0.26 mmol, 0.10 eq) in 10 mL of 1:1 Et2O/NaOH (25% aq) at 0° C. was bubbled 1,1,1,2,2-pentafluoro-2-iodoethane gas for 30 min (>5eq). During this time a UV lamp was directed at the reaction vessel while the temperature was maintained below 10° C. by intermittent use of an ice bath. The contents were then warmed to room temperature, extracted into Et2O (300 mL), dried (MgSO4), and concentrated under reduced pressure. A portion of this crude material was used in subsequent reactions without further purification (200 mg residue: 120 mg product, 0.39 mmol, 1.2 eq).

1. temperaturewas maintained below 10° C. by intermittent use of an ice bath
2. extractionextracted into Et2O (300 mL)
3. dry with materialdried (MgSO4)
4. concentrationconcentrated under reduced pressure
5. customA portion of this crude material was used in subsequent reactions without further purification (200 mg residue: 120 mg product, 0.39 mmol, 1.2 eq)

ORD record

ord-e4503302c26c400aa6fc120a2998e6ae

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680269B2