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

HRID 1941114Notes

Reaction equation

HRID 1941114 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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35]>C(#N)C>[Br:35][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 6342AcetonitrileSolvent

Procedure

A mixture of 10 g of the product obtained in Stage 1 (0.0523 mol), 16.5 g of triphenylphosphine (0.0628 mol), 17.3 g of carbon tetrabromide (0.0628 mol) and 200 ml of acetonitrile is left stirring for 2 hours. The solvent is then evaporated under vacuum and the product purified by chromatography on a silica column, Merck 70-230 mesh, using dichloromethane as eluent.

Workup

  1. waitis left
  2. customThe solvent is then evaporated under vacuum
  3. customthe product purified by chromatography on a silica column, Merck 70-230 mesh

Sources & evidence

ORD record
ord-20399b95160f41c9befc8c8939316f52
Source dataset
uspto-grants-1997_12
Patent number
US05703070

Reaction notes

Loading…