Carbon tetrabromide → 3-(2-bromoethyl)-5-methoxy-1H-indole

HRID 624044Notes

Reaction equation

HRID 624044 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13]O.C(Br)(Br)(Br)[Br:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:16][CH2:13][CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:8][CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 128355-Methoxytryptophol

Product 1

HCID 111078683-(2-bromoethyl)-5-methoxy-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(5-methoxy-1H-indol-3-yl)ethanol (4.0 g, 20.92 mmol) in DCM (30 mL), CBr4 (7.98 g, 24.06 mmol) was added, then the reaction mixture was cooled to 0° C. and PPh3 (6.3 g, 24.0 mmol) was added. After stirring at rt for 2 h, the solvent was removed under reduced pressure. Purification was performed by FC (EtOAc/hex 3:1, Rf=0.31) to yield the title compound as a brown oil which turned into a solid during storage in the freezer. LC-MS conditions B: tR=0.78 min, [M+H]+=254.06.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customPurification

Sources & evidence

ORD record
ord-3b59993991b94bff8ec6e59ba9cf55b2
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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