Bromine → HCID 58072286, compound

HRID 1895123Notes

Reaction equation

HRID 1895123 reaction equation
[C:1]([C:4]1[C:9](=[O:10])[CH:8]=[CH:7][N:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:5]=1)(=[O:3])[CH3:2].[Br:21]Br>CC(O)=O.O.C([O-])(O)=O.[Na+]>[C:1]([C:4]1[C:9](=[O:10])[C:8]([Br:21])=[CH:7][N:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:20])[F:18])[CH:12]=2)[N:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 24408BromineHCID 58072342HCID 58072342, compound

Product 1

HCID 58072286HCID 58072286, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-acetyl-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (1.00 g, 3.54 mmol) in AcOH (3.5 mL) was added Br2 (0.181 mL, 3.54 mmol) at room temperature. The mixture was stirred at room temperature for 2 h. The mixture was diluted with water and NaHCO3 aqueous solution, extracted with EtOAc, dried over MgSO4, filtered, concentrated in vacuo and purified by column chromatography on silica gel (hexane/EtOAc=50/50 to 0/100) to yield the title compound (332 mg, 26% yield) as a pale yellow solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 2.57 (3H, s), 7.79-7.91 (2H, m), 8.09-8:17 (1H, m), 8.22 (1H, s), 9.58 (1H, s).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography on silica gel (hexane/EtOAc=50/50 to 0/100)

Sources & evidence

ORD record
ord-2b3202a0bfbb49e09c7ea45e70b32c81
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

Loading…