4-Iodophenol → HCID 18442679, compound

HRID 1821962Notes

Reaction equation

HRID 1821962 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[C:20]([Cl:22])[Cl:21])[CH:14]=[C:13]([Cl:23])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][O:8]S(C)(=O)=O.[I:24][C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[C:20]([Cl:22])[Cl:21])[CH:14]=[C:13]([Cl:23])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][O:8][C:28]1[CH:29]=[CH:30][C:25]([I:24])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 86602295HCID 86602295, compound

Product 1

HCID 18442679HCID 18442679, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g of methanesulfonic acid 3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propyl ester, 1.14 g of 4-iodophenol and 1.96 g of potassium carbonate are stirred for 24 hours at 50° C. in 20 ml of dimethylformamide. The reaction mixture is poured onto water and extracted with ethyl acetate. The organic phase is washed with water and potassium carbonate solution and concentrated. Purification over silica gel yields 1,3-dichloro-5-(3,3-dichloro-allyloxy)-2-[3-(4-iodo-phenoxy)-propoxy]-benzene. 1H-NMR (CDCl3) 300 MHz: 2.28 (m, 2H), 4.13 (t, 2H), 4.22 (t, 2H), 4.58 (d, 2H), 6.10 (t, 1H), 6.71 (d, 2H), 6.81 (s, 2H), 7.55 (d, 2H)

Workup

  1. additionThe reaction mixture is poured onto water
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water and potassium carbonate solution
  4. concentrationconcentrated
  5. customPurification over silica gel

Sources & evidence

ORD record
ord-b6e400610f7c4b0babeb5ae9fa5ff4ec
Source dataset
uspto-grants-2009_10
Patent number
US07608631B2

Reaction notes

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