Water → 1-(4-Bromobutoxy)-4-iodobenzene

HRID 2120014Notes

Reaction equation

HRID 2120014 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Br:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.O>CN(C=O)C>[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80561,4-DibromobutaneHCID 108944-IodophenolHCID 11430Potassium Carbonate

Product 1

HCID 224822541-(4-Bromobutoxy)-4-iodobenzeneYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 4-iodophenol (100 g, 0.5 mol) and K2CO3 (70 g, 0.5 mol) in DMF (400 mL) was added 1,4 dibromobutane (100 mL, 0.84 mol) over a period of 1 hr. The solution was stirred overnight at room temperature under Ar. H2O (1000 mL) was added and the reaction mixture was extracted with CH2Cl2. The organic layer was then washed with 1000 mL of brine, dried over MgSO4, concentrated to gave a white solid (100 g); 1H NMR (CD3Cl): δ 2.15-1.87 (m, 6H), 3.50-3.20 (m, 4H), 3.94 (t, 2H), 6.85 (d, 2H), 7.55 (d, 2H).

Workup

  1. extractionthe reaction mixture was extracted with CH2Cl2
  2. washThe organic layer was then washed with 1000 mL of brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bb911d52630e48d1a2902df42765a210
Source dataset
uspto-grants-2004_02
Patent number
US06686502B1

Reaction notes

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