Methyl iodide → Ethyl 2,4-dibromo-3-ethoxybenzoate

HRID 841164Notes

Reaction equation

HRID 841164 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+].IC.[CH2:23](N(CC)C=O)[CH3:24]>CN(C=O)C>[Br:1][C:2]1[C:12]([O:13][CH2:23][CH3:24])=[C:11]([Br:14])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12051DiethylformamideHCID 14851207Ethyl 2,4-dibromo-3-hydroxybenzoate

Product 1

HCID 22621032Ethyl 2,4-dibromo-3-ethoxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

Ethyl 2,4-dibromo-3-hydroxybenzoate (5.0 g) was added to a stirred suspension of potassium carbonate (106.4 g) in dry N,N-diethylformamide (DMF). A solution of iodomethane (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-d7dcaf06108f44a48e188a0d70cd0514
Source dataset
uspto-grants-2002_04
Patent number
US06369270B1

Reaction notes

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