Iodoethane → Ethyl 3-bromo-4-chlorobenzoate

HRID 488840Notes

Reaction equation

HRID 488840 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:19][CH3:20]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([O:7][CH2:19][CH3:20])=[O:6]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 27355443-Bromo-4-chlorobenzoic acid

Product 1

HCID 12594300Ethyl 3-bromo-4-chlorobenzoateYield 104.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-bromo-4-chlorobenzoic acid (3.00 g, 12.74 mmol) and cesium carbonate (6.23 g, 19.11 mmol) in acetonitrile (70 mL) was added iodoethane (5.1 mL, 63.7 mmol). The reaction mixture was heated at reflux overnight. After cooling to room temperature, the solution was extracted with ethyl acetate. The organic layer was washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. Choromatography on silica gel (biotage, 5% EtOAc in hexane) afforded 3.5 g of ethyl 3-bromo-4-chlorobenzoate (97%). 1H NMR (300 MHz; CDCl3) 1.40 (t, 3H); 4.37 (q, 2H); 7.52 (d, J=8.1 Hz, 1H); 7.91 (dd, J1=8.4 Hz, J2 =1.8 Hz, 1H); 8.28 (d, J=1.8 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe organic layer was washed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e7f5832c99894304b9ab2f53465a88f8
Source dataset
uspto-grants-2005_12
Patent number
US06974826B2

Reaction notes

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