Triphenylphosphine → 3-(2-bromoethyl)-6-methoxy-1H-indole

HRID 127268Notes

Reaction equation

HRID 127268 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[CH3:22][O:23][C:24]1[CH:32]=[C:31]2[C:27]([C:28]([CH2:33][CH2:34]O)=[CH:29][NH:30]2)=[CH:26][CH:25]=1>C(#N)C.C(OCC)C>[CH3:22][O:23][C:24]1[CH:32]=[C:31]2[C:27]([C:28]([CH2:33][CH2:34][Br:20])=[CH:29][NH:30]2)=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 204851012-(6-Methoxy-1h-indol-3-yl)ethanol

Product 1

HCID 117368993-(2-bromoethyl)-6-methoxy-1H-indole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a mechanically stirred mixture of 18.3 g (69.7 mmol) triphenylphosphine and 200 ml acetonitrile, 11.15 g (69.7 mmol) bromine is added dropwise over 20 minutes. The mixture is stirred 20 minutes at 0° and the ice bath is removed. A solution of 12.1 g (63.4 mmol) 6-methoxy-3-(2-hydroxyethyl)indole in 60 ml acetonitrile is added over 30 minutes. After stirring 2 hours at room temperature the mixture is diluted with 250 ml diethyl ether. The liquid is decanted from precipitated tar. The residue is washed with an additional 250 ml diethyl ether. The volume of the ethereal extracts is reduced to about 60 ml and the solution is filtered through 75 g silica gel with diethyl ether. The solvent is removed to yield 6-methoxy-3-(2-bromoethyl)indole, 4.1 g, yellow waxy solid, mp 98°-101°, which turns green on standing.

Workup

  1. additionis added dropwise over 20 minutes
  2. customthe ice bath is removed
  3. stirringAfter stirring 2 hours at room temperature the mixture
  4. customThe liquid is decanted
  5. customfrom precipitated tar
  6. washThe residue is washed with an additional 250 ml diethyl ether
  7. filtrationthe solution is filtered through 75 g silica gel with diethyl ether
  8. customThe solvent is removed

Sources & evidence

ORD record
ord-1af3e70acf944dccbf459d1421d22719
Source dataset
uspto-grants-1981_03
Patent number
US04255432

Reaction notes

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