Iodoethane → Ethyl 2,4-dibromo-3-ethoxybenzoate

HRID 610754Notes

Reaction equation

HRID 610754 reaction equation
[Br:1][C:2]1[C:12]([OH:13])=[C:11]([Br:14])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].I[CH2:22][CH3:23]>CN(C)C=O>[Br:1][C:2]1[C:12]([O:13][CH2:22][CH3:23])=[C:11]([Br:14])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 14851207Ethyl 2,4-dibromo-3-hydroxybenzoate

Product 1

HCID 22621032Ethyl 2,4-dibromo-3-ethoxybenzoateYield 95.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
85 °C

Procedure

Ethyl 2,4-dibromo-3-hydroxybenzoate (50 g) was added to a stirred suspension of potassium carbonate (106.4 g) in dry N,N-dimethylformamide (DMF). A solution of iodoethane (25.7 g) in DMF was added over 18 minutes, and the resulting mixture was heated at 85° C. for 1.3 hours. The cooled mixture was poured onto water and extracted with ether. The extract was washed (brine solution), dried (anhydrous magnesium sulphate) and the solvent evaporated in vacuo to give ethyl 2,4-dibromo-3-ethoxybenzoate (52.08 g), NMR 1.4(t,3H), 1.5(t,3H), 4.1(q,2H), 4.4(q,2H), 7.35(d,1H), 7.55(d,1H).

Workup

  1. additionThe cooled mixture was poured onto water
  2. extractionextracted with ether
  3. washThe extract was washed (brine solution)
  4. dry with materialdried (anhydrous magnesium sulphate)
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-c7138ba4e7ea4a04ab5b7799472cca77
Source dataset
uspto-grants-1999_12
Patent number
US05998653

Reaction notes

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