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

HRID 1062485Notes

Reaction equation

HRID 1062485 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 (APCI−) 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-3ef37ac073304f6d89977b9d0731403c
Source dataset
uspto-grants-2005_11
Patent number
US06960604B2

Reaction notes

Loading…