Carbon tetrabromide → HCID 69834067, compound

HRID 413800Notes

Reaction equation

HRID 413800 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[Cl:25][C:26]1[CH:27]=[C:28]([CH:47]=[CH:48][C:49]=1[Cl:50])[CH2:29][N:30]1[C:38]2[C:33](=[C:34]([O:39][CH2:40]CO)[CH:35]=[CH:36][CH:37]=2)[CH:32]=[C:31]1[C:43]([O:45][CH3:46])=[O:44]>ClCCl>[Cl:25][C:26]1[CH:27]=[C:28]([CH:47]=[CH:48][C:49]=1[Cl:50])[CH2:29][N:30]1[C:38]2[C:33](=[C:34]([O:39][CH2:40][CH2:20][Br:24])[CH:35]=[CH:36][CH:37]=2)[CH:32]=[C:31]1[C:43]([O:45][CH3:46])=[O:44]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18522138HCID 18522138, compound

Product 1

HCID 69834067HCID 69834067, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (0.55 g) was added in small portions over 2 hours to a stirred solution of carbon tetrabromide (0.47 g) and methyl N-(3,4-diclilorobenzyl)-4-(hydroxyethyloxy)indole-2-carboxylate (0.28 g) in dichloromethane (10 ml). The reaction was stirred for 3 hours at room temperature, concentrated in vacuo and the residue purified by column chromatography using dichloromethane as eluent to give methyl N-(3,4-dichlorobenzyl)-4-(bromoethyloxy)indole-2-carboxylate as a white solid (0.29 g, 90%); NMR d (CD3SOCD3) 3.80 (s, 3H), 3.89 (t, 2H), 4.46 (t, 2H), 5.80 (s, 2H), 6.62 (d, 1H), 6.88 (dd, 1H), 7.17 (d, 1H), 7.25 (t, 1H), 7.30-7.36 (m, 2H), 7.52 (d, 1H), M/z (+) 456, 458 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-395f14b1027c488ab160b9ba1f220333
Source dataset
uspto-grants-2003_05
Patent number
US06569888B1

Reaction notes

Loading…