Iodoethane → 4-Tert-butyl-5-chloro-2-ethoxy-1-iodobenzene

HRID 2425587Notes

Reaction equation

HRID 2425587 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH3:9].[C:10]([C:14]1[C:15]([Cl:22])=[CH:16][C:17]([I:21])=[C:18]([OH:20])[CH:19]=1)([CH3:13])([CH3:12])[CH3:11]>CC(=O)CC>[C:10]([C:14]1[C:15]([Cl:22])=[CH:16][C:17]([I:21])=[C:18]([O:20][CH2:8][CH3:9])[CH:19]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 10881471HCID 10881471, compound

Product 1

HCID 672462864-Tert-butyl-5-chloro-2-ethoxy-1-iodobenzeneYield 85%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (8.0 g, 58.0 mmol) and iodoethane (3.0 mL, 37.7 mmol) were added to a stirred solution of 5-t-butyl-4-chloro-2-iodophenol (2.4 g, 8.1 mmol; prepared according to Fukata et al. Bull. Chem. Soc. Jpn. 1994, 67, 592-594) in 2-butanone (50 mL). The resulting mixture was heated in an oil bath (80° C.) for 16 h and then allowed to cool. The solution was concentrated and redisolved in methylene chloride. The organic layer was washed with water, brine, dried over anhydrous magnesium sulfate and concentrated to give 4-tert-butyl-5-chloro-2-ethoxy-1-iodobenzene (2.2 g, 85%) as a yellow oil.

Workup

  1. temperatureto cool
  2. concentrationThe solution was concentrated
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-84a2d24a72a04221b61e0afe647be97e
Source dataset
uspto-grants-2011_06
Patent number
US07964724B2

Reaction notes

Loading…