p-Toluenesulfonic acid → Methyl 2-(4-fluorophenyl)benzoxazole-4-carboxylate

HRID 2365291Notes

Reaction equation

HRID 2365291 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][C:9]2[C:18]([OH:19])=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=O)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]2[O:19][C:18]3[C:9](=[C:10]([C:11]([O:13][CH3:14])=[O:12])[CH:15]=[CH:16][CH:17]=3)[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 59625786Methyl 2-(4-fluoro-benzoylamino)-3-hydroxy-benzoate

Product 1

HCID 59626027Methyl 2-(4-fluorophenyl)benzoxazole-4-carboxylateYield 55%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Methyl 2-(4-fluoro-benzoylamino)-3-hydroxy-benzoate 9dd (7.4 mmol, 1.2 g crude) and 1.3 g (7.5 mmol) of p-toluenesulfonic acid was refluxed in 10 mL of xylene overnight. After cooling saturated NaHCO3 was added and the resulting mixture was extracted with EtOAc. The organic solvent was evaporated to give 1.1 g (55%) of methyl 2-(4-fluorophenyl)benzo[d]oxazole-4-carboxylate, 9ee. MS m/z (M+H+) 272.0.

Workup

  1. additionwas added
  2. extractionthe resulting mixture was extracted with EtOAc
  3. customThe organic solvent was evaporated

Sources & evidence

ORD record
ord-8a9b58f9907746d181060b7765d336b3
Source dataset
uspto-grants-2014_04
Patent number
US08697684B2

Reaction notes

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