Water → 1,1-Dimethylethyl 4-amino-3-bromo-α-methylbenzeneacetate

HRID 1640016Notes

Reaction equation

HRID 1640016 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O.O>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:6][C:7]=1[Br:17]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 22105824HCID 22105824, compound

Product 1

HCID 574294281,1-Dimethylethyl 4-amino-3-bromo-α-methylbenzeneacetateYield 88.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of tert-butyl 2-(4-aminophenyl)propanoate (5.00 g, 22.6 mmol) in DMF (15 mL) was added a solution of N-bromosuccinimide (4.22 g, 23.7 mmol) in DMF (15 ML) at room temperature which was maintained by water bath. The mixture was stirred overnight, poured into water and extracted with ethyl acetate. The organic layer was separated, washed with water, then brine, dried over sodium sulfate, and filtered. After concentration, the residue was purified by flash chromatography (9:1 hexanes/ethyl acetate) to give tert-butyl 2-(4-amino-3-bromophenyl)propanoate (6.00 g, 85%) as a brown oil: 1H NMR (500 MHz, CDCl3) δ 7.34 (d, J=1.6 Hz, 1H), 7.04 (dd, J=8.1, 1.7 Hz, 1H), 6.71 (d, J=8.2 Hz, 1H), 4.01 (br s, 2H), 3.46 (q, J=7.1 Hz, 1H), 1.39 (m, 12H).

Workup

  1. temperaturewas maintained by water bath
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialbrine, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationAfter concentration
  8. customthe residue was purified by flash chromatography (9:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-07f9b829a24f44dc9cf838f04dbebae7
Source dataset
uspto-grants-2012_02
Patent number
US08110681B2

Reaction notes

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