Sulfuric Acid → 5-Bromo-2-iodo-1,3-diisopropylbenzene

HRID 1618472Notes

Reaction equation

OS(O)(=O)=O.[CH:6]([C:9]1[CH:15]=[C:14]([Br:16])[CH:13]=[C:12]([CH:17]([CH3:19])[CH3:18])[C:10]=1N)([CH3:8])[CH3:7].N([O-])=O.[Na+].[I-:24].[K+]>CC#N.O>[I:24][C:10]1[C:9]([CH:6]([CH3:8])[CH3:7])=[CH:15][C:14]([Br:16])=[CH:13][C:12]=1[CH:17]([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 5 °C

Procedure

To a 2 L 3-neck flask, equipped with mechanical stirrer, thermometer, and additional funnel, added 300 g of ice and 300 mL of H2SO4. 2,6-diisopropyl-4-bromoaniline (46.0 g, 0.18 mol) in 200 mL of CH3CN was added dropwise to this mixture while the temperature was maintained under 5° C. Then sodium nitrite (22.5 g, 0.32 mol) in 180 mL of ice cold water was added dropwise while the temperature was maintained around 0° C. The resulting clear solution was slowly poured into the solution of potassium iodide (105 g, 0.63 mol) in 300 ml of water at room temperature. The mixture was stirred for 1 h. After regular work up, the crude product was distilled at 170° C. under vacuum to afford 1-iodo-2,6-diisopropyl-4-bromobenzene (60 g) as light brown soft solid upon cooling.

Workup

customTo a 2 L 3-neck flask, equipped with mechanical stirrer
temperaturewas maintained around 0° C
distillationAfter regular work up, the crude product was distilled at 170° C. under vacuum

Sources & evidence

ORD record: ord-d86d38bc89074431a15340e0bca9f1fb
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08766529B2

Reaction notes

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