Methanol → Methyl 3-bromo-5-iodobenzoate

HRID 852521Notes

Reaction equation

HRID 852521 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].O=S(Cl)Cl.[CH3:16]O>>[CH3:16][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([I:11])[CH:10]=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 51825203-Bromo-5-iodobenzoic acid

Product 1

HCID 21942573Methyl 3-bromo-5-iodobenzoateYield 97%

Procedure

To a solution of 3-bromo-5-iodo-benzoic acid (D7) (14.6 g, 44.7 mmol, 1 equiv) in MeOH (150 ml) at 0° C. was added SOCl2 (3.9 ml, 53.6 mmol, 1.2 equiv). The resulting solution was refluxed for 2 h, cooled to room temperature and concentrated in vacuo. The residue was diluted with AcOEt and washed twice with 2N aqueous NaOH solution then brine, dried over MgSO4 and concentrated in vacuo to give 3-bromo-5-iodo-benzoic acid methyl ester (D8a) (14.8 g, 97%) as a pale brown solid.

Workup

  1. temperatureThe resulting solution was refluxed for 2 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with AcOEt
  4. washwashed twice with 2N aqueous NaOH solution
  5. dry with materialbrine, dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-646fc9eaac2f4dd99bd9c5566b2f3643
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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