Iodine → Benzoic acid, 4-iodo-2-methoxy-, methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7](N)=[CH:6][C:5]=1[O:11][CH3:12].S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:23].[K+].II>O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([I:23])=[CH:6][C:5]=1[O:11][CH3:12]Participants
Procedure
4-Amino-2-methoxybenzoic acid methyl ester (3.0 g, 16.6 mmol) was suspended in water (40 mL) and concentrated sulfuric acid (10 mL) was added. The suspension was cooled in an ice/salt water bath, and an aqueous solution (10 mL) of sodium nitrite (1.26 g, 18.3 mmol) was added dropwise so that the temperature remained close to 0° C. After the addition, a homogeneous, yellow-green solution was obtained. An aqueous solution (60 mL) of potassium iodide (3.02 g, 18.2 mmol) and iodine (2.31 g, 9.1 mmol) was then added dropwise, and the reaction stirred for an additional 1 hour. The reaction mixture was then extracted with ethyl acetate, the organic extracts were combined and washed with 1 N sodium thiosulfate, 1 N sodium hydroxide and brine. After drying over anhydrous sodium sulfate the solution was filtered and concentrated in vacuo to give 2.7 g of the title product as an orange oil which was used in the next step.
Workup
- temperatureThe suspension was cooled in an ice/salt water bath
- customremained close to 0° C
- additionAfter the addition
- customa homogeneous, yellow-green solution was obtained
- extractionThe reaction mixture was then extracted with ethyl acetate
- washwashed with 1 N sodium thiosulfate, 1 N sodium hydroxide and brine
- dry with materialAfter drying over anhydrous sodium sulfate the solution
- filtrationwas filtered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-7a0548905a324fa286ae916810f0d4b6
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109193B2
Reaction notes
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