Tryptophol → 3-(2-Bromoethyl)indole

HRID 1506938Notes

Reaction equation

HRID 1506938 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11]O)=[CH:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:32]C(Br)(Br)Br>ClCCl>[Br:32][CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

5

Reactant 3

HCID 10685TryptopholHCID 11205Carbon tetrabromideHCID 11776Triphenylphosphine

Product 1

HCID 769243-(2-Bromoethyl)indoleYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(indol-3-yl)ethanol (623 mg, 3.86 mmol) was dissolved in dichloromethane (20 mL) and the solution was cooled to 0° C. Triphenylphosphine (1.12 g, 4.25 mmol) and tetra-bromomethane (1.41 g, 4.25 mmol) were then added thereto, followed by stirring for 1 hour. After the reaction was completed, the reaction mixture was concentrated under reduced pressure to remove the solvent. The resulting residue was purified by column chromatography to afford the title compound (765 mg, 88%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto remove the solvent
  3. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-119f434f23da4adbb77969ba12056e97
Source dataset
uspto-grants-2015_12
Patent number
US09221790B2

Reaction notes

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