Carbon tetrabromide → 5-Fluoro-indolyl-3-propylbromide

HRID 1954221Notes

Reaction equation

HRID 1954221 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2CCCO.[C:15]([Br:19])(Br)(Br)Br.[C:20]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:21]=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH:15]([Br:19])[CH2:20][CH3:21])=[CH:5]2

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 150205413-(5-fluoro-1H-indol-3-yl)propan-1-ol2×

Product 1

HCID 540585145-Fluoro-indolyl-3-propylbromideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(5-fluoro-1H-indol-3-yl)-propan-1-ol (Intermediate 6) prepared in accordance with the procedures set forth in Demerson et al., J. Med. Chem., 19:391-395 (1976). (25.4 g, 0.13 mol), carbon tetrabromide (65.5 g, 0.2 mol) and triphenylphosphine (52 g, 0.2 mol) in methylene chloride (156 ml) was allowed to stir for 2 hours. The solvent was evaporated and the product chromatographed (30% ethyl acetate-hexanes) to afford 33.5 g (99%) of product.

Workup

  1. customThe solvent was evaporated
  2. customthe product chromatographed (30% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-d4053f703fe24a289bfd1acf2f51dd38
Source dataset
uspto-grants-2000_09
Patent number
US06121307

Reaction notes

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