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

HRID 1280449Notes

Reaction equation

HRID 1280449 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-cd862cb7714045efa5d985070c476127
Source dataset
uspto-grants-2002_09
Patent number
US06451801B1

Reaction notes

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