Acetic Acid → 2-Fluoro-3-methylphenol
Reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.C(O)(=[O:14])C.OO>O1CCCC1>[F:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-fluoro-3-methyl-phenylboronic acid (25.0 g, 0.162 mol) in tetrahydrofuran (220 mL) was added glacial acetic acid (150 mL). The resulting mixture was cooled to 0° C. before hydrogen peroxide (50% aqueous solution, 30 mL) was added. The resulting mixture was allowed to come to room temperature and stirred for 24 h. The mixture was evaporated and the residue was dissolved in ethyl acetate, washed with hydrochloric acid (0.5N), water and brine. The organic phase was dried, filtered and evaporated which afforded 2-fluoro-3-methyl-phenol (20.0 g, 98%) as an oil.
Workup
- additionwas added
- customto come to room temperature
- customThe mixture was evaporated
- dissolutionthe residue was dissolved in ethyl acetate
- washwashed with hydrochloric acid (0.5N), water and brine
- customThe organic phase was dried
- filtrationfiltered
- customevaporated which
Sources & evidence
- ORD record
- ord-aa5c5e78742844bdae149513bb04dc08
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741327B2
Reaction notes
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