Acetone → 2-{3-Fluoro-4-[2-methoxyvinyl]phenyl}propan-2-ol

HRID 385704Notes

Reaction equation

[CH3:1][O:2][CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][C:6]=1[F:12].C([Li])CCC.[CH3:18][C:19]([CH3:21])=[O:20].O>O1CCCC1>[F:12][C:6]1[CH:7]=[C:8]([C:19]([OH:20])([CH3:21])[CH3:18])[CH:9]=[CH:10][C:5]=1[CH:4]=[CH:3][O:2][CH3:1]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of compound 2-(4-bromo-2-fluorophenyl)vinyl methyl ether (115.5 g, 0.5 mol) in tetrahydrofuran (666 mL) at −78° C. was added n-butyllithium (240 mL of 2.5M in hexanes, 0.6 mol), and the resulting mixture was stirred at −78° C. for 1 hour. A solution of acetone (37.7 g, 0.65 mol) in tetrahydrofuran (283 mL) was added dropwise to the reaction mixture. Then the reaction solution was slowly warmed to 0° C., stirred for 30 minutes, and then at room temperature for 30 minutes. Water (300 mL) was added to quench the reaction. The biphasic mixture was extracted with ethyl acetate (2×). The combined organics were dried and concentrated in vacuo. Purification via flash chromatography afforded the title compound.

Workup

temperatureThen the reaction solution was slowly warmed to 0° C.
stirringstirred for 30 minutes
waitat room temperature for 30 minutes
customto quench
customthe reaction
extractionThe biphasic mixture was extracted with ethyl acetate (2×)
customThe combined organics were dried
concentrationconcentrated in vacuo
customPurification via flash chromatography

Sources & evidence

ORD record: ord-deb57b2d65864e3d8ad86f7076dbd954
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367706B2

Reaction notes

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