2,6-Dibromo-4-nitrophenol → HCID 67495580, compound

HRID 1952526Notes

Reaction equation

HRID 1952526 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Br:11])[C:3]=1[OH:12].[C:13](=[O:16])([O-])[O-].[K+].[K+].BrCCCCCC[C:26]1[CH:36]=[CH:35][CH:34]=[C:28]2[C:29]([NH:31][C:32](=[O:33])[C:27]=12)=O>C(#N)C>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Br:11])[C:3]=1[O:12][CH2:4][CH2:3][CH2:2][CH2:7][CH2:6][CH2:29][N:31]1[C:32](=[O:33])[C:27]2[C:26](=[CH:36][CH:35]=[CH:34][CH:28]=2)[C:13]1=[O:16]

Participants

5

Reactant 3

HCID 74292,6-Dibromo-4-nitrophenolHCID 11430Potassium CarbonateHCID 219308536-Bromohexylphthalimide

Product 1

HCID 67495580HCID 67495580, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,6-dibromo-4-nitrophenol (2.00 g, 6.74 mmol) in acetonitrile (10 mL) was added potassium carbonate (2.79 g, 20.22 mmol). The resulting mixture was stirred for 0.5 h under reflux conditions. To this was added 6-bromohexylphthalimide (2.30 g, 7.41 mmol) and continued stirring for another 72 hours at 80° C. The reaction mixture was cooled to room temperature and filtered through Celite. The filtrate was concentrated in vacuo. MPLC purification (Hexanes:EtOAc/80:20) of the residue gave 12 as a white amorphous solid (1.10 g, 60%). 1H NMR (400 MHz, CDCl3) δ 8.38 (s, 2H), 7.82-7.84 (m, 2H), 7.69-7.72 (m, 2H), 4.07 (t, J=6.4 Hz, 2H), 3.70 (t, J=7.2 Hz, 2H), 1.87-1.91 (m, 2H), 1.72-1.75 (m, 2H), 1.58-1.62 (m, 2H), and 1.43-1.47 (m, 2H).

Workup

  1. stirringcontinued stirring for another 72 hours at 80° C
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customMPLC purification (Hexanes:EtOAc/80:20) of the residue

Sources & evidence

ORD record
ord-6efb5610a518471fb29f883c1b5b28b0
Source dataset
uspto-grants-2013_03
Patent number
US08404728B2

Reaction notes

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