Potassium Iodide → HCID 71015404, compound

HRID 2207477Notes

Reaction equation

N([O-])=O.[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([CH:19]=[CH:20][C:21]=1[Cl:22])[O:9][C:10]1[CH:16]=[CH:15][C:13](N)=[CH:12][C:11]=1[O:17][CH3:18].[I-:23].[K+]>O.S(=O)(=O)(O)O>[Cl:22][C:21]1[CH:20]=[CH:19][C:8]([O:9][C:10]2[CH:16]=[CH:15][C:13]([I:23])=[CH:12][C:11]=2[O:17][CH3:18])=[CH:7][C:6]=1[Cl:5]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of sodium nitrite (14.4 g, 208.70 mmol, 1.98 equiv) in water (500 mL) was added dropwise into a solution of 4-(3,4-dichlorophenoxy)-3-methoxyaniline (30 g, 105.58 mmol, 1.00 equiv) in sulfuric acid (1000 mL) with stirring at 0° C. and the mixture was stirred for 30 min at 0° C. The above mixture was added dropwise to a solution of potassium iodide (1000 mL, 5%) in water with stirring at 50° C. The reaction was completed immediately. The reaction mixture was cooled to room temperature, extracted with ethyl acetate and the organic layers combined. The resulting mixture was washed with saturated aqueous sodium bicarbonate and brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum to give 24 g (crude) of 1,2-dichloro-4-(4-iodo-2-methoxyphenoxy)benzene as a red oil.

Workup

stirringthe mixture was stirred for 30 min at 0° C
stirringwith stirring at 50° C
temperatureThe reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate
washThe resulting mixture was washed with saturated aqueous sodium bicarbonate and brine
dry with materialThe mixture was dried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-3aa487685d6944d2a93cace36c0f1fe7
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376438B2

Reaction notes

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