Methanol → Methyl 3-bromo-5-iodobenzoate

HRID 1805348Notes

Reaction equation

HRID 1805348 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 75%

Procedure

To a suspension of 3-bromo-5-iodo-benzoic acid (6.5 g, 20 mmol) in 25 mL of methanol was added SOCl2 (1.14 mL, 40 mmol) dropwise at 0° C. The mixture was then warmed to room temperature and stirred at room temperature for 2 days. The precipitates formed were collected by filtration to afford the desired product as white solid 5.12 g (75%). LC/MS m/e calcd. for C8H6BrIO2: 341, observed (M+H)+: 342.2.

Workup

  1. customThe precipitates formed
  2. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-32570e99c3a04d1584097f08b37e8732
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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