Chlorobenzene → 4-(4-Chlorobenzoyl)-5-methylisoxazole

HRID 342943Notes

Reaction equation

HRID 342943 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[O:10][N:9]=[CH:8][C:7]=1[C:11](Cl)=[O:12].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:11]([C:7]2[CH:8]=[N:9][O:10][C:6]=2[CH3:5])=[O:12])=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 7964ChlorobenzeneHCID 27599175-Methyl-1,2-oxazole-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 539796794-(4-Chlorobenzoyl)-5-methylisoxazole

Conditions

Temperature
80 °C

Procedure

A mixture of aluminium chloride (16 g) and 5-methylisoxazole-4-carbonyl chloride (5.0 g) in dry chlorobenzene (50 ml) was stirred in an atmosphere of nitrogen for 16 hours. The mixture was heated to 80° C. for 1 hours. The cooled mixture was quenched with excess ice and extracted with ethyl acetate (3×200 ml). The combined organic layers were washed with water (3×500 ml), dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness. The residue was purified by chromatography on silica eluted with a mixture of ethyl acetate and cyclohexane (1:20) to give 4-(4-chlorobenzoyl)-5-methylisoxazole (compound 9, 5.2 g) as a yellow solid mp 65°-66° C.

Workup

  1. customThe cooled mixture was quenched with excess ice
  2. extractionextracted with ethyl acetate (3×200 ml)
  3. washThe combined organic layers were washed with water (3×500 ml)
  4. dry with materialdried (anhydrous magnesium sulphate)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customThe residue was purified by chromatography on silica
  8. washeluted with a mixture of ethyl acetate and cyclohexane (1:20)

Sources & evidence

ORD record
ord-1f148e2a8c404b51b9c046f630d2b31f
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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