Chlorosuccinimide → 6-bromo-3-chloro-1H-indole

HRID 331039Notes

Reaction equation

HRID 331039 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C1C(=O)N([Cl:18])C(=O)C1>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([Cl:18])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 6764936-Bromoindole

Product 1

HCID 122699216-bromo-3-chloro-1H-indoleYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 6-bromo-1H-indole (850 mg, 4.34 mmol) and NCS (593 mg, 4.44 mmol) in DCM (17 mL) was stirred at 0° C. for 1.5 hour. The mixture was partitioned between saturated aqueous ammonium chloride (25 mL) and ethyl acetate (150 mL). The organic phase was separated, washed with brine (25 mL), dried with anhydrous magnesium sulfate, filtered and evaporated to dryness to give the title compound (894 mg). LCMS (A): m/z (M+H)+ 230/232, C8H5BrClN requires 229/231 (acidic).

Workup

  1. customThe mixture was partitioned between saturated aqueous ammonium chloride (25 mL) and ethyl acetate (150 mL)
  2. customThe organic phase was separated
  3. washwashed with brine (25 mL)
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-bd6a1b5d738a42c79cab82c7df2d9c8b
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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