Carbon tetrabromide → 1H-Indole, 5-bromo-3-(2-bromoethyl)-

HRID 2184822Notes

Reaction equation

HRID 2184822 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]2[CH2:30][CH2:31]O.C(Br)(Br)(Br)[Br:34]>ClCCl>[Br:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]2[CH2:30][CH2:31][Br:34]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1229565-Bromo-1H-indole-3-ethanol

Product 1

HCID 183997061H-Indole, 5-bromo-3-(2-bromoethyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 11.5 g of triphenylphosphine in 60 ml of dichloromethane is added to a solution, cooled to 0° C., of 4 g of the compound obtained in Step 1 and 7.5 g of carbon tetrabromide in 100 ml of dichloromethane. After stirring for 48 hours at ambient temperature, the reaction mixture is concentrated in vacuo. The residue obtained is chromatographed on silica gel (dichloromethane/cyclohexane: 80/20), enabling the expected product to be isolated.

Workup

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. customThe residue obtained
  3. customis chromatographed on silica gel (dichloromethane/cyclohexane: 80/20)
  4. customto be isolated

Sources & evidence

ORD record
ord-490ad3aae54f4bef8d6f7d1f68fa186d
Source dataset
uspto-grants-2002_06
Patent number
US06399616B1

Reaction notes

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