Potassium Iodide → 3-{3-[2,2,2-Trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-propan-1-ol

HRID 1452688Notes

Reaction equation

[F:1][C:2]([F:26])([F:25])[C:3]([C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1)([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[C:4]([F:7])([F:6])[F:5].Br[CH2:28][CH2:29][CH2:30][OH:31].C([O-])([O-])=O.[Cs+].[Cs+].[I-].[K+]>CC(C)=O>[F:1][C:2]([F:25])([F:26])[C:3]([C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=1)[O:24][CH2:28][CH2:29][CH2:30][OH:31])([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)[C:4]([F:6])([F:5])[F:7]

Participants

Conditions

Temperature: 50 °C

Procedure

1.12 g (2.9 mmol) of 3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenol (example 5) in 20 ml of acetone were treated with 0.51 mL (5.9 mmol) of 3-bromo-1-propanol in the presence of 1.9 g (5.9 mmol) Cs2CO3 and 245 mg (1.5 mmol) of potassium iodide. The reaction mixture was stirred at 50° C. overnight, filtered and evaporated. The crude product was redissolved in EtOAc and a 1M KHSO4 solution, the phases were separated and the inorganic one extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and the solvent was evaporated. Column chromatography on silica gel yielded 1.1 g (84%) of 3-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-propan-1-ol as a colorless liquid, MS: 438 (M)+.

Workup

filtrationfiltered
customevaporated
dissolutionThe crude product was redissolved in EtOAc
customa 1M KHSO4 solution, the phases were separated
extractionthe inorganic one extracted with EtOAc
washThe combined organic phases were washed with brine
dry with materialdried (Na2SO4)
customthe solvent was evaporated

Sources & evidence

ORD record: ord-fd4337e66af04e8db153d5e49c0be58f
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473705B2

Reaction notes

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