Acetone → 2-{3,5-Difluoro-4-[2-methoxyvinyl]phenyl}propan-2-ol
Reaction equation
[CH3:1][O:2][CH:3]=[CH:4][C:5]1[C:10]([F:11])=[CH:9][C:8](Br)=[CH:7][C:6]=1[F:13].[Li]CCCC.[CH3:19][C:20]([CH3:22])=[O:21].O>C(OC)(C)(C)C>[F:13][C:6]1[CH:7]=[C:8]([C:20]([OH:21])([CH3:22])[CH3:19])[CH:9]=[C:10]([F:11])[C:5]=1[CH:4]=[CH:3][O:2][CH3:1]Participants
6
Conditions
- Temperature
- -78 °C
Procedure
To a cooled (−78° C.) solution of 2-(4-bromo-2,6-difluorophenyl)vinyl methyl ether (45 g, 0.18 mol) in methyl tert-butyl ether (300 mL) was added n-BuLi (75 mL of 2.5M in hexanes, 0.19 mol), and the mixture was stirred at −78° C. for one hour. A solution of acetone (13.6 g, 0.24 mol) in methyl tert-butyl ether (100 mL) was added dropwise to the reaction mixture and the resulting solution was stirred at −78° C. for two hours. Water (90 ml) was added to quench the reaction. The resulting biphasic mixture was extracted with ethyl acetate (2×). The organic layers were dried and concentrated in vacuo. Purification via flash chromatography afforded the title compound.
Workup
- stirringthe resulting solution was stirred at −78° C. for two hours
- customto quench
- customthe reaction
- extractionThe resulting biphasic mixture was extracted with ethyl acetate (2×)
- customThe organic layers were dried
- concentrationconcentrated in vacuo
- customPurification via flash chromatography
Sources & evidence
- ORD record
- ord-1fa293a6fad04ebeaa21820e49e76a12
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367706B2
Reaction notes
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