Selectfluor → Methyl 5-fluoro-6-hydroxynaphthalene-1-carboxylate
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=[CH:5]2.[B-](F)(F)(F)[F:17].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C.C(OCC)(=O)C>[F:17][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]([O:14][CH3:15])=[O:13]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 85 °C
Procedure
To a stirred solution of methyl 6-hydroxy-1-naphthoate (25 g, 123.8 mmol) in anhydrous acetonitrile (130 mL), SelectFluor (45 g, 127.5 mmol) was added and the reaction vessel sealed (sealed tube). The reaction mixture was heated to 85° C. for 3 d. The reaction mixture was allowed to cool to RT, diluted with ethyl acetate and washed with water, then brine, dried with Na2SO4, filtered and evaporated. The mixture was purified by column chromatography using methylene chloride as the eluent. The title compound was obtained as a tan solid.
Workup
- customthe reaction vessel sealed
- custom(sealed tube)
- temperatureto cool to RT
- washwashed with water
- dry with materialbrine, dried with Na2SO4
- filtrationfiltered
- customevaporated
- customThe mixture was purified by column chromatography
Sources & evidence
- ORD record
- ord-b43d0d7d09c1476f8bddcd14619abc56
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178557B2
Reaction notes
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