Potassium Iodide → HCID 67059833, compound

HRID 601450Notes

Reaction equation

[CH3:1][C@@H:2]([CH2:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[CH2:3][CH2:4][C:5]1[CH:11]=[CH:10][C:8](N)=[CH:7][CH:6]=1.[N+]([O-])([O-])=O.[Na+].[I-:23].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>Cl.O.CCOCC>[I:23][C:8]1[CH:10]=[CH:11][C:5]([CH2:4][CH2:3][C@@H:2]([CH3:1])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 4-[(3S)-3,7-dimethyl-6-octenyl]aniline (10.0 g, 43.2 mmol, Example 4) in concentrated HCl (9 mL) and water (100 mL) was cooled to 0° C. and then a solution of sodium nitrate (NaNO2, 2.96 g, 43.2 mmol) in water (22 mL) was added dropwise. To the resulting arenediazonium salt a solution of potassium iodide (7.11 g, 43.2 mmol) in water (22 mL) was added dropwise and the mixture was heated at 40° C. for 2 hours. Sodium thiosulfate was added and the suspension was extracted with ether (3×50 mL) and the combined organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to give a dark oil. The crude material was dissolved in ether and filtered through a plug of silica gel to give 1-iodo-4-[(3S)-3,7-dimethyl-6-octenyl]benzene as a colorless oil (9.27 g, 27.1 mmol, 62.5% yield).

Workup

temperaturethe mixture was heated at 40° C. for 2 hours
extractionthe suspension was extracted with ether (3×50 mL)
washthe combined organic phase was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customto give a dark oil
filtrationfiltered through a plug of silica gel

Sources & evidence

ORD record: ord-05dd9f4fbc94462a81a716f71388fcfa
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902363B2

Reaction notes

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