Ethanol → Ethyl 5-Bromo-2-iodobenzoate

HRID 503957Notes

Reaction equation

HRID 503957 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:12](Cl)(=O)[C:13](Cl)=O.CCO>C(Cl)Cl>[CH2:12]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[I:11])[CH3:13]

Participants

5

Reactant 3

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 3029395-Bromo-2-iodobenzoic acid

Product 1

HCID 10338259Ethyl 5-Bromo-2-iodobenzoateYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

5-Bromo-2-iodo-benzoic acid (25.0 g, 76.47 mol) was dissolved in CH2Cl2 (75 ml) at room temperature. Oxalyl chloride (14.5 ml, 152.94 mmol) was added and the mixture was stirred at 40° C. for 30 minutes. The mixture was allowed to cool to room temperature and EtOH (6.69 ml, 114.71 mmol) was added. The mixture was concentrated under reduced pressure to give 27.2 g (quantitative) of 5-bromo-2-iodo-benzoic acid ethyl ester as a yellow crystalline solid.

Workup

  1. temperatureto cool to room temperature
  2. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-312cf3a871e34176871076776dcd3da6
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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