2-Amino-6-fluorophenol → Methyl 7-fluorobenzo[d]oxazole-2-carboxylate

HRID 390778Notes

Reaction equation

HRID 390778 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]=1

Participants

4

Reactant 2

HCID 6435622-Amino-6-fluorophenolHCID 12586559Methyl 2,2,2-trimethoxyacetate

Product 1

HCID 59536124Methyl 7-fluorobenzo[d]oxazole-2-carboxylateYield 53.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. customformed
  2. filtrationFiltration
  3. washby washing with MeOH

Sources & evidence

ORD record
ord-49ad6aa55667485fb6fcd57a13fec7bb
Source dataset
uspto-grants-2013_02
Patent number
US08383670B2

Reaction notes

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