Phosphorus oxychloride → 1-(4-bromophenyl)-5-chloro-3-(2-chloro-6-fluorophenyl)-1H-1,2,4-triazole

HRID 508720Notes

Reaction equation

HRID 508720 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=O)[NH:11][C:10]([C:14]3[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])=[N:9]2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:24]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([Cl:24])=[N:11][C:10]([C:14]3[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1366448592-(4-bromophenyl)-5-(2-chloro-6-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 900274831-(4-bromophenyl)-5-chloro-3-(2-chloro-6-fluorophenyl)-1H-1,2,4-triazole

Procedure

To 2-(4-bromophenyl)-5-(2-chloro-6-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (Intermediate-1, 0.100 g, 0.271 mmol) was added POCl3. The reaction mass was refluxed for 48 h. The reaction mass was quenched in water, basified with NaHCO3 and extracted with ethyl acetate and concentrated. The obtained crude product was purified with column chromatography on silica gel eluting with 0.5% EA:DCM to afford 0.110 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 7.44 (t, J=9.3 Hz, 1H), 7.53 (d, J=7.8 Hz, 1H), 7.60-7.68 (m, 1H), 7.72 (d, J=9.0 Hz, 2H), 7.85 (d, J=8.7 Hz, 2H). MS (m/z): 388.22 (M+H)+.

Workup

  1. temperatureThe reaction mass was refluxed for 48 h
  2. customThe reaction mass was quenched in water
  3. extractionextracted with ethyl acetate
  4. concentrationconcentrated
  5. customThe obtained crude product
  6. customwas purified with column chromatography on silica gel eluting with 0.5% EA

Sources & evidence

ORD record
ord-bb5ec6132503434298c1ebb62d89504d
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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