N-bromobutanimide → 3,6-Dibromo-1-(3-methoxypropyl)-1H-indole

HRID 656237

Reaction equation

HRID 656237 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH2:13][O:14][CH3:15])=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O>O1CCCC1>[Br:16][C:6]1[C:5]2[C:9](=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=2)[N:8]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 231516746-Bromo-1-(3-methoxypropyl)-1H-indole

Product 1

HCID 686528323,6-Dibromo-1-(3-methoxypropyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 10.39 g of 6-bromo-1-(3-methoxypropyl)-1H-indole (building block 5) in 1.5 l of tetrahydrofuran is cooled to −78° C., and 7.05 g of N-bromosuccinimide are added. The mixture is stirred at −78° C. for 1.7 hours and then warmed to room temperature. The reaction mixture is evaporated. The title compound is obtained as an orange oil from the residue by flash chromatography (SiO2 60 F). Rf=0.31 (EtOAc-heptane 1:4); Rt=5.65 (Gradient I).

Workup

  1. temperaturewarmed to room temperature
  2. customThe reaction mixture is evaporated

Sources & evidence

ORD record
ord-c69ef97162fb406ab0133ecdbc96b27e
Source dataset
uspto-grants-2011_12
Patent number
US08071651B2

Linked notes

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