Acetic Acid → 2-Iodo-4-nitrobenzoic acid

HRID 968278Notes

Reaction equation

[I-].[K+].[I:3]([C:5]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])=O.C(O)(=O)C>O>[I:3][C:5]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

Conditions

Temperature: 23 °C

Procedure

Solid potassium iodide (55 g, 0.33 mol) was added in one portion to a suspension of 2-iodosyl-4-nitro-benzoic acid I-1a (54.9 g, 0.18 mol) in water (250 ml) and glacial acetic acid (50 ml). Over the next 5-10 minutes, the solids gradually went into solution and the solution turned from off-white to red. After stirring for one hour at 23° C., gaseous sulfur dioxide was bubbled through the reaction mixture until the red color dissipated and a pale green suspension had formed. The solids were collected by filtration, co-evaporated from toluene (3×250 ml), and dried in vacuo to affort 2-iodo-4-nitrobenzoic acid I-1b (33 g, 64%).

Workup

customOver the next 5-10 minutes
customgaseous sulfur dioxide was bubbled through the reaction mixture until the red color
customa pale green suspension had formed
filtrationThe solids were collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-3c96c164c96c4e5680b852debc230534
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06958347B2

Reaction notes

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