1-Bromo-3-chloropropane → 1-(3-Chloropropoxy)-4-iodobenzene

HRID 1669730Notes

Reaction equation

HRID 1669730 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[CH2:16][CH2:17][CH2:18][Cl:19]>CC(=O)CC>[Cl:19][CH2:18][CH2:17][CH2:16][O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 108944-IodophenolHCID 11430Potassium Carbonate

Product 1

HCID 158955201-(3-Chloropropoxy)-4-iodobenzene

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of p-iodophenol (20 g, 91 mmol), potassium carbonate (25.2 g, 182 mmol) and 1-bromo-3-chloropropane (commercially available, for example, from Aldrich) (18 g, 114 mmol) in anhydrous 2-butanone (300 ml) was heated at reflux for 72 h, cooled to room temperature, filtered and evaporated to dryness. The resulting residue was purified by SPE filtration (70 g silica cartridge, eluting with 20:1 cyclohexane-ethyl acetate) to afford the title compound (24.9 g); 1H NMR (CDCl3) δ 7.5 (2H, d), 6.7 (2H, d), 4.1 (2H, t), 3.8 (2H, t), 2.2 (2H, q).

Workup

  1. temperatureat reflux for 72 h
  2. filtrationfiltered
  3. customevaporated to dryness
  4. filtrationThe resulting residue was purified by SPE filtration (70 g silica cartridge, eluting with 20:1 cyclohexane-ethyl acetate)

Sources & evidence

ORD record
ord-a4284733ba5f4ffaa3d4880495956e61
Source dataset
uspto-grants-2011_08
Patent number
US07989629B2

Reaction notes

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