Dichloromethane → Methyl 5-bromoindoline-7-carboxylate

HRID 562008Notes

Reaction equation

HRID 562008 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 the title compound as a brown solid (6.5 g).

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-f4319135c6c54e3ba7a307dcd6527d52
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

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