Pyridine → HCID 54557372, compound

HRID 266507Notes

Reaction equation

HRID 266507 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 1.5 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-e225159bd58240f9be08c51321d13bc6
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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