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

HRID 1755006Notes

Reaction equation

HRID 1755006 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

5

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 123831174-Bromo-3,5-dimethylanilineHCID 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%).

Workup

  1. customthe mixture was irradiated with microwaves at 130° C. for 15 minutes
  2. washthe organic layer was sequentially washed with water and saturated brine
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-af07f6c631204295bde8a89d1d35aab7
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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