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

HRID 507085Notes

Reaction equation

HRID 507085 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 esterYield 102.5%

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) (Example 48, Step 3) 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 saturated NaHCO3 and brine and dry over sodium sulfate. Remove the solvent under reduced pressure to afford the title compound (3.10 g, quantitative). MS (ES+): 271 (M+H).

Workup

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

Sources & evidence

ORD record
ord-08519d28d6f4453b88d4d48e78022c1d
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

Loading…