Water → 1-(4-(trifluoromethoxy)phenyl)-3-(4-vinylphenyl)-1 H-1,2,4-triazole

HRID 924207Notes

Reaction equation

HRID 924207 reaction equation
N1(C2CCCCCCCCCC2)CCCN=CCCCC[CH2:2]1.[F:23][C:24]([F:46])([F:45])[O:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH:36]=[N:35][C:34]([C:37]3[CH:44]=[CH:43][C:40]([CH:41]=O)=[CH:39][CH:38]=3)=[N:33]2)=[CH:28][CH:27]=1.O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[F:23][C:24]([F:46])([F:45])[O:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH:36]=[N:35][C:34]([C:37]3[CH:44]=[CH:43][C:40]([CH:41]=[CH2:2])=[CH:39][CH:38]=3)=[N:33]2)=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 962WaterHCID 578244624-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzaldehydeHCID 1296629601,8-Diazabicycloundec-7ene

Product 1

HCID 904049191-(4-(trifluoromethoxy)phenyl)-3-(4-vinylphenyl)-1 H-1,2,4-triazoleYield 69.8%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Methyltriphenylphosphonium bromide (32.2 g, 90.0 mmol) and 1,8-diazabicycloundec-7-ene (14.9 mL, 99.0 mmol) were dissolved in tetrahydrofuran (260 mL) and refluxed for 30 minutes. 4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzaldehyde (15.0 g, 45.0 mmol) was added, and the reaction was heated at 65° C. for 5 hours. The solution was cooled and stirred at room temperature overnight. The reaction mixture was poured into water and extracted with hexanes. The organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated. The crude compound was purified by flash column chromatography using 0-70% ethyl acetate/hexanes as eluent to afford the title compound as a white solid (10.4 g, 67%): 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.16 (d, J=8.3 Hz, 2H), 7.80 (d, J=9.0 Hz, 2H), 7.58-7.47 (m, 2H), 7.39 (d, J=9.1 Hz, 2H), 6.77 (dd, J=17.6, 10.9 Hz, 1H), 5.84 (dd, J=17.6, 0.8 Hz, 1H), 5.32 (dd, J=10.9, 0.8 Hz, 1H); 19F NMR (376 MHz, CDCl3) δ −58.02; ESIMS m/z 332 ([M+H]+).

Workup

  1. temperaturerefluxed for 30 minutes
  2. temperatureThe solution was cooled
  3. extractionextracted with hexanes
  4. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude compound was purified by flash column chromatography

Sources & evidence

ORD record
ord-ecabfe8141f9434a90f44878d2ac4909
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

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