N-bromobutanimide → Ethyl 2-(4-amino-3-bromophenyl)acetate

HRID 1773973Notes

Reaction equation

HRID 1773973 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[Br:14]N1C(=O)CCC1=O>CC#N>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[C:7]([Br:14])[CH:6]=1)[CH3:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 19702145Ethyl 2-(4-amino-3-bromophenyl)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 4-aminophenylacetate (1.79 g, 10 mmol, 1 eq.) in MeCN (50 mL), N-bromsuccinimide (1.78 g, 10 mmol, 1 eq.) was added slowly. The mixture was stirred at r.t. for 72 hours. The reaction mixture was concentrated in vacuo. The residue was partitioned between water (50 mL) and Et2O (50 mL). The org. phase was washed with sat. aq. NaCl soln. (1×50 mL), dried over MgSO4, and concentrated in vacuo to give (4-amino-3-bromo-phenyl)-acetic acid ethyl ester as an orange oil. The product was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between water (50 mL) and Et2O (50 mL)
  3. washphase was washed with sat. aq. NaCl soln
  4. dry with material(1×50 mL), dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e986737d4dab4274bb71e2f7d4a0cac2
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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