Pyridine → HCID 54557372, compound

HRID 2256891Notes

Reaction equation

HRID 2256891 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-nitro4-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 magnesia 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 magnesia sulphate)
  4. filtrationfiltered
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-d6c415f9b03440de853a72edc2bdbd7a
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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