Ethyl Acetate → 4-Amino-7-bromo-indan-5-carboxylic acid methyl ester

HRID 2353959Notes

Reaction equation

HRID 2353959 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]([C:13]1[C:14]([NH2:22])=[C:15]2[C:19](=[CH:20][CH:21]=1)[CH2:18][CH2:17][CH2:16]2)=[O:12].C(OCC)(=O)C>C(O)(=O)C>[CH3:9][O:10][C:11]([C:13]1[C:14]([NH2:22])=[C:15]2[C:19](=[C:20]([Br:1])[CH:21]=1)[CH2:18][CH2:17][CH2:16]2)=[O:12]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 593791394-Amino-indan-5-carboxylic acid methyl ester

Product 1

HCID 593791324-Amino-7-bromo-indan-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Add N-bromosuccinimide (1.99 g, 11.2 mmol) to 4-Amino-indan-5-carboxylic acid methyl ester (2.15 g, 11.2 mmol) in acetic acid (13 mL). Stir the mixture at room temperature for 48 h. Pour the mixture into ice-water and add ethyl acetate. Separate the layers and wash the organic phase with sat NaHCO3 and brine and dry over sodium sulfate. Remove the solvent under reduced pressure to afford the title compound (3.10, quantitative). MS (ES+): 271 (M+H).

Workup

  1. customSeparate the layers
  2. washwash the organic phase with sat NaHCO3 and brine
  3. dry with materialdry over sodium sulfate
  4. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-a92e157fd02f4c3581a3f2c3a106307c
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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