Lithium Hydroxide → 5-(4-Bromophenyl)oxazole-4-carboxylic acid

HRID 919047Notes

Reaction equation

HRID 919047 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[CH:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)=[O:5])C.[OH-].[Li+].C(Cl)Cl>CO.O>[Br:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]2[O:9][CH:8]=[N:7][C:6]=2[C:4]([OH:5])=[O:3])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 6344DichloromethaneHCID 2758809Ethyl 5-(4-bromophenyl)oxazole-4-carboxylate

Product 1

HCID 616374135-(4-Bromophenyl)oxazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

5-(4-Bromo-phenyl)-oxazole-4-carboxylic acid ethyl ester (1.0 g, 3.4 mmol) was dissolved in MeOH:H2O (5:1, 60 mL) and then lithium hydroxide (1.0 g, 41.8 mmol) was added. The reaction was heated to 60° C. for 10 minutes then allowed to cool. The reaction was submitted to acidic aqueous/CH2Cl2 workup then concentrated to afford the title compound.

Workup

  1. temperatureto cool
  2. concentrationthen concentrated

Sources & evidence

ORD record
ord-c16d6bb7c8324ea0a6d92a7ae523c21b
Source dataset
uspto-grants-2016_03
Patent number
US09272990B2

Reaction notes

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