Iodine → 5-Chloro-4-iodo-2-methoxybenzoic acid

HRID 588874Notes

Reaction equation

N[C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.S(=O)(=O)(O)O.N([O-])=O.[Na+].[I:23]I>O>[Cl:11][C:10]1[C:2]([I:23])=[CH:3][C:4]([O:12][CH3:13])=[C:5]([CH:9]=1)[C:6]([OH:8])=[O:7]

Participants

Conditions

Temperature: 5 °C

Procedure

To a stirred solution of 4-amino-5-chloro-2-methoxybenzoic acid (5 g, 24.8 mmol) in water (10 mL) at 0° C., concentrated sulfuric acid (50 mL) was added. Then a solution of NaNO2 (1.9 g, 27.3 mmol) in water (10 mL) was added dropwise while keeping the internal temperature around 0° C. KI (4.5 g, 27.3 mmol) and I2 (3.5 g, 13.64 mmol) were dissolved in water and added dropwise to the stirred reaction mixture. The reaction was stirred at 5° C. for 2 h and then extracted with ethyl acetate. The organic layer was washed with water, Na2SO3 (aq, 10%) and brine, dried over anhydrous Na2SO4 and concentrated in vacuo to afford desired product (1.55 g, 19% yield). ESI-MS m/z: 311.1[M+H]+.

Workup

customthe internal temperature around 0° C
additionadded dropwise to the stirred reaction mixture
extractionextracted with ethyl acetate
washThe organic layer was washed with water, Na2SO3 (aq, 10%) and brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-03ec96ce21844c67afa3ff12321484c3
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227978B2

Reaction notes

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