Phosphorus tribromide → 3-(3-bromopropyl)-1H-indole

HRID 1461704Notes

Reaction equation

HRID 1461704 reaction equation
P(Br)(Br)[Br:2].O[CH2:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1>CCOCC>[Br:2][CH2:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 77115Indole-3-propanol

Product 1

HCID 100371923-(3-bromopropyl)-1H-indoleYield 15%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
23 °C

Procedure

Phosphorus tribromide (17.4 g) in Et2O)30 mL) was added dropwise to a Et2O solution (100 mL) containing 3-(3-hydroxypropyl)indole (VI; 7.5 g) at 0° C. with stirring and under N2 atmosphere. After the addition was complete, the reaction was allowed to warm to 23° C. and continuously stirred for 16 h. At the end of this time, the reaction was cooled to 0° C. and ice (ca. 25 mL) added portionwise and stirred an additional 2 h. The organic phase was separated from the aqueous phase and the aqueous layer extracted with Et2O. The combined organic phases were washed with sat. NaCl solution, dried with MgSO4, filtered, and concentrated under reduced pressure to afford 3-(3-bromopropyl)indole (V; 1.51 g; 15%).

Workup

  1. additionAfter the addition
  2. stirringcontinuously stirred for 16 h
  3. temperatureAt the end of this time, the reaction was cooled to 0° C.
  4. stirringstirred an additional 2 h
  5. customThe organic phase was separated from the aqueous phase
  6. extractionthe aqueous layer extracted with Et2O
  7. washThe combined organic phases were washed with sat. NaCl solution
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b38eb981c1734bc4a25f3a86c3f548c9
Source dataset
uspto-grants-1991_12
Patent number
US05077293

Reaction notes

Loading…