2-bromo-1-(4-bromo-3-nitrophenyl)ethanone → HCID 67985759, compound

HRID 539776Notes

Reaction equation

HRID 539776 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[N:12][C:11]([NH2:14])=[CH:10][CH:9]=1.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([Br:25])=[C:21]([N+:26]([O-:28])=[O:27])[CH:20]=1)=O>C(#N)C>[Br:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[N:14]=[C:11]3[CH:10]=[CH:9][C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])=[N:13][N:12]3[CH:16]=2)=[CH:20][C:21]=1[N+:26]([O-:28])=[O:27]

Participants

4

Reactant 2

HCID 122241662-bromo-1-(4-bromo-3-nitrophenyl)ethanoneHCID 457878336-(2-fluorophenyl)pyridazin-3-amine

Product 1

HCID 67985759HCID 67985759, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 6-(2-fluorophenyl)pyridazin-3-amine (2.22 g, 11.7 mmol) and 2-bromo-1-(4-bromo-3-nitrophenyl)ethanone (3.78 g, 11.7 mmol) in acetonitrile (100 mL) is heated at 80° C. for 12 hours. The mixture is concentrated to dryness and then purified via chromatography using CH2Cl2 to afford the title compound (1.83 g, 37%) as a yellow solid: Rf 0.46 (CH2Cl2); LCMS (m/z)=413.3, 415.3 [M+H]+, tR=3.19 min.

Workup

  1. concentrationThe mixture is concentrated to dryness
  2. custompurified via chromatography

Sources & evidence

ORD record
ord-7400d62615e14da1ac3a660a21574acc
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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