Acetic Acid → 1-Iodo-2,4-dimethyl-3-nitrobenzene

HRID 239919Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N+:9]([O-:11])=[O:10].S(=O)(=O)(O)O.C(O)(=O)C.[I:21]I>O>[I:21][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[C:4]=1[CH3:8]

Participants

Conditions

Temperature: 90 °C

Procedure

To 1,3-dimethyl-2-nitro-benzene (68.5 g, 453.2 mmol) is added sulfuric acid (27.2 mL, 510 mmol), acetic acid (543.8 mL, 9.49 mol), iodine (46 g, 181.3 mmol) and HIO4 (91.9 g, 403.3 mmol). The reaction is heated to 90° C. for 7 days. The reaction mixture is cooled to ambient temperature and water (500 mL) is added. The resulting solid is collected by filtration and washed with cold water. The solid is dried under reduced pressure at 45° C. overnight to afford the title compound as a yellow solid (119 g, 95%). 1H NMR (300.16 MHz, CDCl3): δ 7.80 (d, J=8.2 Hz, 1H), 6.85 (d, J=8.2 Hz, 1H), 2.37 (s, 3H), 2.23 (s, 3H).

Workup

temperatureThe reaction mixture is cooled to ambient temperature
filtrationThe resulting solid is collected by filtration
washwashed with cold water
customThe solid is dried under reduced pressure at 45° C. overnight

Sources & evidence

ORD record: ord-d0b62ca0fd454239a7d154c07cd94bce
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642768B2

Reaction notes

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