Anisole → 2'-Fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-thiol

HRID 1049433Notes

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]([S:16]CC2C=CC(OC)=CC=2)=[CH:12][C:11]=1[CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28].C1(OC)C=CC=CC=1.[OH-].[Na+]>FC(F)(F)C(O)=O>[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]([SH:16])=[CH:12][C:11]=1[CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of (2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-yl)(4-methoxybenzyl)sulfane (1.68 g) in trifluoroacetic acid (6.6 mL) was added anisole (2.15 mL) at room temperature, and the mixture was stirred at 90° C. for 8 hr. The reaction mixture was cooled to 0° C., neutralized with 8N aqueous sodium hydroxide solution, and 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 (NH, ethyl acetate/hexane) to give the title compound (918 mg) as a pale-yellow oil.

Workup

temperatureThe reaction mixture was cooled to 0° C.
extractionextracted 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 (NH, ethyl acetate/hexane)

Sources & evidence

ORD record: ord-138e27c3cab543ad8ae50c3180ef6f9d
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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