Sodium Bicarbonate → 2'-Fluoro-2-(1-fluoro-3,3-dimethylbutyl)-5'-methoxy-4-((4-methoxybenzyl)oxy)biphenyl

HRID 1049586Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21](OC)=[CH:20][CH:19]=2)=[CH:12][C:11]=1[CH:26](O)[CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29].C(C1C=C(C)C(S(F)(F)[F:45])=C(C)C=1)(C)(C)C.[C:49](=[O:52])([O-])O.[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:52][CH3:49])=[CH:20][CH:19]=2)=[CH:12][C:11]=1[CH:26]([F:45])[CH2:27][C:28]([CH3:30])([CH3:31])[CH3:29]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-yl)-3,3-dimethylbutan-1-ol (220 mg) in toluene (5 mL) was added 4-(tert-butyl)-2,6-dimethylphenylsulfur trifluoride (188 mg) at 0° C., and the mixture was stirred at 0° C. for 20 min. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (180 mg) as a colorless oil.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-e5e1f550820c4ab9a733d3a72a8b84f6
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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