Hydrochloric Acid → Methyl 3-bromo-5-iodobenzoate

HRID 2216751Notes

Reaction equation

HRID 2216751 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([OH:7])=[O:6].Cl.[CH3:13]O>C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([O:7][CH3:13])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 51825203-Bromo-5-iodobenzoic acid

Product 1

HCID 21942573Methyl 3-bromo-5-iodobenzoateYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of, 3-bromo-5-iodobenzoic acid (9.0 g) in methanol (40 mL) was treated with 1M HCl in diethyl ether (27.5 mL). The reaction was heated overnight at 40° C. The solvent was then removed in vacuo, and the residue dissolved in ethyl acetate. The organic solution was washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and concentrated to afford 8.8 g (94%) of methyl 3-bromo-5-iodobenzoate.

Workup

  1. customThe solvent was then removed in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic solution was washed with saturated sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cfa815205dff4271bdb0f0fe66b5a2a7
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

Loading…