Iodine → Methyl 3-iodo-4-methoxy-5-nitrobenzoate

Reaction equation

N[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[I:17]I.N(OC(C)(C)C)=O>C1(C)C=CC=CC=1>[I:17][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6]

Participants

Procedure

To a solution of methyl 3-amino-4-(methyloxy)-5-nitrobenzoate (D163) (370 mg, 1.64 mmol, 1 equiv) in toluene (20 ml) at 0° C. was added iodine (218 mg, 0.86 mmol, 0.5 equiv) then 1,1-dimethylethyl nitrite (200 mg, 1.75 mmol, 1.1 equiv) and the resulting mixture was stirred at room temperature for 15 h then partitioned between AcOEt and brine. The two layers were separated and the organic phase was dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel gave methyl 3-iodo-4-(methyloxy)-5-nitrobenzoate (D165) (280 mg, 51%) as a light brown solid. No molecular ion. RT=3.33 min.