Iodoethane → 1-(5-Chloro-2-ethoxy-3-iodo-4-methylphenyl)ethanone

HRID 1499691Notes

Reaction equation

HRID 1499691 reaction equation
[Cl:1][C:2]1[C:3]([CH3:13])=[C:4]([I:12])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.I[CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CCOCC>[Cl:1][C:2]1[C:3]([CH3:13])=[C:4]([I:12])[C:5]([O:11][CH2:15][CH3:16])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 114723941-(5-Chloro-2-hydroxy-3-iodo-4-methylphenyl)ethanone

Product 1

HCID 866668651-(5-Chloro-2-ethoxy-3-iodo-4-methylphenyl)ethanoneYield 91.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1-(5-Chloro-2-hydroxy-3-iodo-4-methylphenyl)ethanone (18.9 g, 60.9 mmol) (from Example 1, Step 1) was dissolved in N,N-dimethylformamide (60.8 mL). Iodoethane (7.3 mL, 91 mmol) was added followed by potassium carbonate (17 g, 120 mmol). The reaction was heated at 60° C. for 1 hour. The mixture was cooled to room temperature, diluted with ether. The organic layers were combined, washed with water, dried over MgSO4, concentrated and purified on silica gel (eluting with 0-10% EtOAc in hexanes) to give the desired product (18.9 g, 91.7%). LCMS calculated for C11H13ClIO2 (M+H)+: m/z=339.0; Found: 339.0.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. custompurified on silica gel (eluting with 0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f4a9bd7c8c894782b8a337878300d3ad
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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