Potassium Iodide → HCID 71015404, compound

HRID 1854886Notes

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 3×500 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×500 mL of saturated aqueous sodium bicarbonate and 3×500 mL of 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 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 3×500 mL of ethyl acetate
washThe resulting mixture was washed with 3×500 mL of saturated aqueous sodium bicarbonate and 3×500 mL of brine
dry with materialThe mixture was dried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-f56f08999b6c447f8af2eaa196cdfe79
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962831B2

Reaction notes

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