2-Amino-6-fluorophenol → Methyl 7-fluorobenzo[d]oxazole-2-carboxylate
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].[CH3:10][O:11][C:12](OC)([O:17]C)[C:13](OC)=O>CO>[F:8][C:4]1[C:3]2[O:9][C:13]([C:12]([O:11][CH3:10])=[O:17])=[N:1][C:2]=2[CH:7]=[CH:6][CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-amino-6-fluorophenol (14) (254 mg, 2 mmol) and methyl 2,2,2-trimethoxyacetate (15) (328 mg, 2 mmol) in 3 ml MeOH was heated in micro wave reactor at 140° C. for 1 h. After cooling down to r.t. crystals formed. Filtration followed by washing with MeOH furnished 208 mg of methyl 7-fluorobenzoxazole-2-carboxylate (16) as brown needles. Yield: 53.3%. LC-MS: calculated M=195.15; observed M=195.96.
Workup
- customformed
- filtrationFiltration
- washby washing with MeOH
Sources & evidence
- ORD record
- ord-bb2edee9777e4c80854a58022966e88a
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07906553B2
Reaction notes
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