Pyridine → HCID 54557372, compound

HRID 342954Notes

Reaction equation

HRID 342954 reaction equation
O[CH:2]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22])[C:3]1[CH:4]=[N:5][O:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1.P(Br)(Br)[Br:25].N1C=CC=CC=1>CCOCC>[Br:25][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22])[C:3]1[CH:4]=[N:5][O:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 54050151HCID 54050151, compound

Product 1

HCID 54557372HCID 54557372, compoundYield 116.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-[hydroxy-(2-nitro-4-trifluoromethylphenyl)methyl]-5-cyclopropylisoxazole (1.0 g), phosphorus tribromide (0.70 g) and pyridine (0.05 g) in dry ether was stirred at 0° C. for 15 hours. The reaction mixture was quenched with water and extracted with ether. The organic extracts were dried (anhydrous magnesium sulphate), filtered and the solvent evaporated yielding 4-[bromo-(2-nitro-4-trifluoromethylphenyl)methyl]-5-cyclopropylisoxazole (compound 299, 1.18 g) as a yellow oil: NMR: (CDCl3) 1.1(4H,m) 1.9(1H,m) 6.9(1H,s) 7.9(1H,m) 8.0(1H,s) 8.15(2H,m).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ether
  3. dry with materialThe organic extracts were dried (anhydrous magnesium sulphate)
  4. filtrationfiltered
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-07a2243501694799a42f8f3e83f47049
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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