Boron tribromide → 5-[4-(4-Hydroxy-3-isopropyl-phenoxy)-3,5-dimethyl-phenyl]-2,4-dihydro-[1,2,4]triazol-3-one

HRID 1168104Notes

Reaction equation

HRID 1168104 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][C:24]=1[O:25]C)[O:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([C:15]2[NH:16][C:17](=[O:20])[NH:18][N:19]=2)=[CH:10][C:9]=1[CH3:21])([CH3:3])[CH3:2].B(Br)(Br)Br>C(Cl)(Cl)Cl>[OH:25][C:24]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[C:13]([CH3:14])=[CH:12][C:11]([C:15]3[NH:16][C:17](=[O:20])[NH:18][N:19]=3)=[CH:10][C:9]=2[CH3:21])=[CH:5][C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 1355559405-[4-(3-Isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-2,4-dihydro-[1,2,4]triazol-3-one

Product 1

HCID 1354861505-[4-(4-Hydroxy-3-isopropyl-phenoxy)-3,5-dimethyl-phenyl]-2,4-dihydro-[1,2,4]triazol-3-oneYield 95.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of the title compound of Step B (4.7 mg, 0.013 mmol) in chloroform (0.5 ml) was added boron tribromide (1M in dichloromethane, 0.26 ml, 0.26 mmol) and the mixture was stirred at room temperature for about one hour. The reaction was quenched with water (5 ml), acidified with 1N HCl (1 ml), and extracted with ethyl acetate (3×10 ml). The combined organic extracts were dried, filtered, and concentrated to afford the title compound (4.2 mg). MS (APCl−) Calc: 339.2, Found: 338.3 (M−1).

Workup

  1. customThe reaction was quenched with water (5 ml)
  2. extractionextracted with ethyl acetate (3×10 ml)
  3. customThe combined organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2c3caa055e9d4e09812fd3fdf3a82360
Source dataset
uspto-grants-2003_09
Patent number
US06620830B2

Reaction notes

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