N-bromobutanimide → 1-Tert-butyl 7-methyl 5-bromoindoline-1,7-dicarboxylate

HRID 562007Notes

Reaction equation

HRID 562007 reaction equation
[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([O:12][CH3:13])=[O:11])[CH2:3][CH2:2]1.[Br:21]N1C(=O)CCC1=O>ClCCl>[Br:21][C:6]1[CH:5]=[C:4]2[C:9](=[C:8]([C:10]([O:12][CH3:13])=[O:11])[CH:7]=1)[N:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:2][CH2:3]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 497588571-Tert-butyl 7-methyl indoline-1,7-dicarboxylate

Product 1

HCID 497588561-Tert-butyl 7-methyl 5-bromoindoline-1,7-dicarboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(1,1-dimethylethyl) 7-methyl 2,3-dihydro-1H-indole-1,7-dicarboxylate (3.1 g, 11.2 mmol) and N-bromosuccinimide (2.0 g, 11.2 mmol) were dissolved in dry dichloromethane (100 mL) and stirred under a nitrogen atmosphere at room temperature for 16 hours. The reaction was partitioned with sodium hydroxide solution (2 M), separated and washed with more sodium hydroxide solution. The organic layer was dried over magnesium sulfate and concentrated in vacuo to give the title compound as a gummy red solid (3.55 g).

Workup

  1. customThe reaction was partitioned with sodium hydroxide solution (2 M)
  2. customseparated
  3. washwashed with more sodium hydroxide solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-630d134d786c4515b9e3e7eb258db42f
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

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