Hydrochloric Acid → 1,3-Benzoxazole-6-carboxylic acid

HRID 1945472Notes

Reaction equation

HRID 1945472 reaction equation
C[O:2][C:3]([C:5]1[CH:23]=[CH:22][C:8]2[N:9]=[C:10](COC3C=CC(Cl)=CC=3Cl)[O:11][C:7]=2[CH:6]=1)=[O:4].[Br-].[Al+3].[Br-].[Br-].O.Cl>CSC.ClCCl>[O:11]1[C:7]2[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:23]=[CH:22][C:8]=2[N:9]=[CH:10]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 166749BromhydrolHCID 24966183HCID 24966183, compound

Product 1

HCID 222459381,3-Benzoxazole-6-carboxylic acidYield 61.2%

Reagents, catalysts & solvents 2

HCID 1068Dimethyl SulfideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,4-dichloro-phenoxymethyl)-benzoxazole-6-carboxylic acid methyl ester (100 mg, 0.29 mmol) in dimethyl sulfide (8 ml) and dichloromethane (58 ml) was added aluminum bromide (1.24 g, 4.64 mmol). The reaction mixture was stirred at room temperature for 2.5 h, after which water and 10% HCl were added. After stirring at room temperature for 1 h, the mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (CH2Cl2:MeOH=4:1) to give 2-2,4-dichloro-phenoxymethyl)-benzoxazole-6-carboxylic acid as a white solid (59.15 mg mg, 61.2% yield).

Workup

  1. stirringAfter stirring at room temperature for 1 h
  2. customthe mixture was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4 anh)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash column chromatography (CH2Cl2:MeOH=4:1)

Sources & evidence

ORD record
ord-645829389c114d89bacf00c999693a37
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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