Potassium Iodide → HCID 14851223, compound

HRID 1494677Notes

Reaction equation

HRID 1494677 reaction equation
[Br:1][C:2]1[C:12]([OH:13])=[C:11]([N+:14]([O-:16])=[O:15])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH3:23][O:24][CH2:25][CH2:26]Cl.[I-].[K+]>CN(C)C=O>[Br:1][C:2]1[C:12]([O:13][CH2:26][CH2:25][O:24][CH3:23])=[C:11]([N+:14]([O-:16])=[O:15])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl etherHCID 14851222HCID 14851222, compound

Product 1

HCID 14851223HCID 14851223, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Using a procedure similar to that of Example 2, 0.2 moles of ethyl 2-bromo-3-hydroxy-4-nitrobenzoate and an excess of potassium carbonate (0.35 moles) and 2-chloroethyl methyl ether (0.35 moles) along with a catalytic amount of potassium iodide (7.2 g, 0.045 m) were combined with 350 ml of dimethylformamide. After heating at 70° C. for 4 hours, normal workup gave 0.187 moles of ethyl 2-bromo-3-(2-methoxyethoxy)-4-nitrobenzoate as a viscous oil. This ester can be readily hydrolyzed to its acid using the procedure of Example 8.

Sources & evidence

ORD record
ord-f5585cdabf444f09b061083b9a037382
Source dataset
uspto-grants-1991_06
Patent number
US05026896

Reaction notes

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