Dichloromethane → Methyl 5-bromoindoline-7-carboxylate

HRID 656004Notes

Reaction equation

HRID 656004 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]2.ClCCl.[OH-].[Na+]>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[NH:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 497588561-Tert-butyl 7-methyl 5-bromoindoline-1,7-dicarboxylate

Product 1

HCID 49758858Methyl 5-bromoindoline-7-carboxylateYield 101.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-(1,1-dimethylethyl) 7-methyl 5-bromo-2,3-dihydro-1H-indole-1,7-dicarboxylate (9 g, 25 mmol) was dissolved in trifluoroacetic acid (6 mL) and stirred at room temperature for 16 hours. Dichloromethane and sodium hydroxide solution (2 M) were added and the organic layer washed twice with sodium hydroxide solution until the aqueous layer pH>7. The organic layer was then concentrated in vacuo to give 6.5 g (100%) of the title compound as a brown solid.

Workup

  1. washthe organic layer washed twice with sodium hydroxide solution until the aqueous layer pH>7
  2. concentrationThe organic layer was then concentrated in vacuo

Sources & evidence

ORD record
ord-099ff6aa91e24915995443e388cabac1
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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