Iodoethane → Ethyl 4-bromo-3-ethoxybenzoate

HRID 2102892Notes

Reaction equation

HRID 2102892 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[OH:13].C(=O)([O-])[O-].[K+].[K+].I[CH2:21][CH3:22]>CN(C=O)C>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 12134897Ethyl 4-bromo-3-hydroxybenzoate

Product 1

HCID 57804236Ethyl 4-bromo-3-ethoxybenzoateYield 62.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 4-bromo-3-hydroxybenzoate (prepared according to M. I. Dawson et al WO 2003048101; 0.5 g, 2.04 mmol), potassium carbonate (0.84 g, 6.12 mmol) and iodoethane (0.2 mL, 2.45 mmol) were placed in 50 mL DMF and the reaction was heated at 80° C. for 18 h. The mixture was cooled and partitioned between EtOAc and water. The organic layer was separated, washed with water, brine, dried (Na2SO4), filtered, and the filtrate was concentrated under vacuum to an oil. The oil was purified by column chromatography using EtOAc/hexane (0-50%) as eluent to give the product (0.35 g, 62%) as a clear oil.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between EtOAc and water
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under vacuum to an oil
  8. customThe oil was purified by column chromatography

Sources & evidence

ORD record
ord-1b5892d5f81848ef9f58b40d43333966
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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