Isopropyl iodide → HCID 117665979, compound

HRID 526778Notes

Reaction equation

HRID 526778 reaction equation
I[CH:2]([CH3:4])[CH3:3].[Cl:5][C:6]1[CH:11]=[C:10]([I:12])[CH:9]=[C:8]([Cl:13])[C:7]=1[OH:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[Cl:5][C:6]1[CH:11]=[C:10]([I:12])[CH:9]=[C:8]([Cl:13])[C:7]=1[O:14][CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 44930832,6-dichloro-4-iodophenol

Product 1

HCID 117665979HCID 117665979, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-iodopropane (3.7 g, 21.77 mmol, 1.00 equiv), 2,6-dichloro-4-iodophenol (5 g, 17.31 mmol, 0.80 equiv) and potassium carbonate (9.2 g, 66.09 mmol, 3.04 equiv) in N,N-dimethylformamide (50 mL) was stirred for overnight at 50° C. The resulting solution was diluted with 300 mL of ethyl acetate then washed with 3×100 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with petroleum ether (100%) to give 4.6 g (64%) of 1,3-dichloro-5-iodo-2-isopropoxybenzene as a light yellow oil. 1H-NMR (300 MHz, CDCl3): δ 7.60 (s, 2H), 4.63-4.54 (m, 1H), 1.34 (d, J=5.1 Hz, 6H) ppm.

Workup

  1. washthen washed with 3×100 mL of brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified on a silica gel column
  5. washeluted with petroleum ether (100%)

Sources & evidence

ORD record
ord-bd8fb95468124d2eaea361a85e8c91d6
Source dataset
uspto-grants-2016_05
Patent number
US09346761B2

Reaction notes

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