Carbon tetrabromide → 3-(3-bromopropyl)-5-fluoro-1H-indole

HRID 1793863Notes

Reaction equation

HRID 1793863 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]2[CH2:11][CH2:12][CH2:13]O.C(Br)(Br)(Br)[Br:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:16][CH2:13][CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)[NH:7][CH:6]=1

Participants

5

Reactant 3

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

Product 1

HCID 114026013-(3-bromopropyl)-5-fluoro-1H-indoleYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(5-fluoro-1H-indol-3-yl)-propan-1-ol (2.15 g, 11.2 mmol), carbon tetrabromide (4.80 g, 14.5 mmol) and triphenylphosphine (4.40 g, 16.7 mmol) in methylene chloride is stirred for 1 h and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, EtOAc/hexane 3/7) to afford the title product as an oil, 1.97 g (69% yield), identified by NMR and mass spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue is purified by flash chromatography (silica gel, EtOAc/hexane 3/7)

Sources & evidence

ORD record
ord-90fc187da0504c148cfea64112170aeb
Source dataset
uspto-grants-2006_04
Patent number
US07022701B2

Reaction notes

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