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

HRID 1019006Notes

Reaction equation

HRID 1019006 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-7759c659a3cf4ed1aa458bb618732ca1
Source dataset
uspto-grants-2002_11
Patent number
US06486171B2

Reaction notes

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