Ethyl Acetate → Ethyl 2-[(4-bromo-3,5-dimethyl-phenyl)amino]-2-methyl-propanoate

Reaction equation

C([CH2:3][C:4](Br)([CH3:8])[C:5]([OH:7])=[O:6])C.C(=O)(O)[O-].[Na+].[Br:15][C:16]1[C:22]([CH3:23])=[CH:21][C:19]([NH2:20])=[CH:18][C:17]=1[CH3:24].[C:25](OCC)(=O)[CH3:26]>>[Br:15][C:16]1[C:22]([CH3:23])=[CH:21][C:19]([NH:20][C:4]([CH3:3])([CH3:8])[C:5]([O:7][CH2:25][CH3:26])=[O:6])=[CH:18][C:17]=1[CH3:24]

Participants

Reactant 4

HCID 8857Ethyl Acetate

HCID 516892Sodium Bicarbonate

HCID 123831174-Bromo-3,5-dimethylaniline

HCID 219158932-Bromo-2-methylpentanoic acid

Product 1

HCID 66818529Ethyl 2-[(4-bromo-3,5-dimethyl-phenyl)amino]-2-methyl-propanoateYield 29%

Procedure

Ethyl-2-bromoisobutyric acid (3.7 ml, 24.99 mmol) and sodium bicarbonate (630 mg, 7.49 mmol) were added to 4-bromo-3,5-dimethyl-aniline (500 mg, 2.49 mmol), and the mixture was irradiated with microwaves at 130° C. for 15 minutes. The reaction mixture was diluted with ethyl acetate, and the organic layer was sequentially washed with water and saturated brine and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give ethyl 2-[(4-bromo-3,5-dimethyl-phenyl)amino]-2-methyl-propanoate (230 mg, 29%).