m-Chloroperbenzoic acid → 3-(4-(7-oxabicyclo[4.1.0]heptan-1-yl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

HRID 1772532Notes

Reaction equation

HRID 1772532 reaction equation
[C:1]1([C:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=2)[CH:6]=[CH:5][C:4]([C:7]2[N:11]=[CH:10][N:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[N:8]=2)=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:34]>C(OCC)C>[C:23]12([C:1]3[CH:2]=[CH:3][C:4]([C:7]4[N:11]=[CH:10][N:9]([C:12]5[CH:13]=[CH:14][C:15]([O:18][C:19]([F:20])([F:21])[F:22])=[CH:16][CH:17]=5)[N:8]=4)=[CH:5][CH:6]=3)[O:34][CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 904116523-(2',3',4',5'-tetrahydro-[1,1'-biphenyl]-4-yl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

Product 1

HCID 904128703-(4-(7-oxabicyclo[4.1.0]heptan-1-yl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazoleYield 77.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 3-(2′,3′,4′,5′-tetrahydro-[1,1′-biphenyl]-4-yl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (CB10) (3.11 g, 8.07 mmol) in diethyl ether (60 mL) was added meta-chloroperoxybenzoic acid (70%; 2.79 g, 11.3 mmol) slowly at 0° C. The reaction was stirred and allowed to gradually warm to room temperature, then stirring was continued for 18 hours. The solution was diluted in diethyl ether, washed with sodium bicarbonate, extracted with diethyl ether, washed with water, and extracted again with diethyl ether. The organics were dried, filtered, and concentrated providing the title compound as a white solid (2.5 g, 77%) which was used without further purification: 1H NMR (400 MHz, CDCl3) δ 8.58 (s, 1H), 8.20-8.11 (m, 2H), 7.84-7.77 (m, 2H), 7.52-7.46 (m, 2H), 7.39 (dt, J=8.0, 1.0 Hz, 2H), 3.12 (dd, J=3.1, 1.7 Hz, 1H), 2.34 (ddd, J=14.9, 8.5, 5.3 Hz, 1H), 2.09-1.95 (m, 2H), 1.74-1.45 (m, 4H), 1.42-1.28 (m, 1H); 19F NMR (376 MHz, CDCl3) δ −58.03; ESIMS m/z 402 ([M+H]+).

Workup

  1. stirringstirring
  2. washwashed with sodium bicarbonate
  3. extractionextracted with diethyl ether
  4. washwashed with water
  5. extractionextracted again with diethyl ether
  6. customThe organics were dried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d62ccc658d4445dc8a3395a35cb7e5dc
Source dataset
uspto-grants-2016_02
Patent number
US09249133B2

Reaction notes

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