Hydrochloric Acid → 2-(4-Fluorophenyl)benzoxazole-4-carboxylic acid

HRID 401639Notes

Reaction equation

HRID 401639 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([O:19]C)=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([OH:19])=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59626027Methyl 2-(4-fluorophenyl)benzoxazole-4-carboxylate

Product 1

HCID 596260302-(4-Fluorophenyl)benzoxazole-4-carboxylic acidYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.1 g (4.0 mmol) methyl 2-(4-fluorophenyl)benzo[d]oxazole-4-carboxylate 9ee and 3.7 mL of 3N aqueous NaOH in 10 mL of THF was refluxed overnight. After cooling the reaction mixture was poured into water and acidified with conc. HCl. The resulting solid was filtered and dried to give 830 mg (79%) of 2-(4-fluorophenyl)-benzo[d]oxazole-4-carboxylic acid, 9ff. MS m/z (M+H+) 258.1.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling the reaction mixture
  3. filtrationThe resulting solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-19dde0fd30694b26a7ef030228da877b
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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