Bromine → 3-Bromo-1-(P-toluenesulfonyl)indole

HRID 2042941Notes

Reaction equation

HRID 2042941 reaction equation
[S:1]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[Br:20]Br>C(Cl)Cl>[Br:20][C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]([S:1]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=2)(=[O:2])=[O:3])[CH:12]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 10956616N-Tosylindole

Product 1

HCID 112102743-Bromo-1-(P-toluenesulfonyl)indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 82 (13 g, 47.9 mmol) in methylene chloride (100 mL) at 0° C. was added bromine (2.7 mL, 52.7 mmol) dropwise. After reaction complete, the resulting solution was evaporated under reduced pressure. The residue was quenched with saturated Na2S2O4 solution, work-up with Et2O. After evaporation of volatile solvent, the title compound was obtained by trituration with hexane.

Workup

  1. customAfter reaction complete
  2. customthe resulting solution was evaporated under reduced pressure
  3. customThe residue was quenched with saturated Na2S2O4 solution, work-up with Et2O
  4. customAfter evaporation of volatile solvent

Sources & evidence

ORD record
ord-ce3bd86a370f48ff86fbdba0a99c7837
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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