2-Bromoethanol → HCID 86728228, compound

HRID 1776800Notes

Reaction equation

HRID 1776800 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:3]=1.[Br:18][CH2:19][CH2:20]O.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:20][CH2:19][Br:18])=[C:4]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:3]=1

Participants

6

Reactant 4

HCID 108982-BromoethanolHCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 13163448HCID 13163448, compound

Product 1

HCID 86728228HCID 86728228, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-bromo-2-(1H-indol-2-yl)phenol (1.44 g, 5 mmol) and 2-bromoethanol (1.12 g, 9 mmol) in 20 mL of THF was added DBAD (2.07 g, 9 mmol) followed by triphenylphosphine (2.36 g, 9 mmol) in portions at room temperature with stirring. After 1 hour, the reaction was concentrated to near dryness, and purified using flash column chromatography (hexane/EtOAc 30:1) to provide the crude product of 2-(5-bromo-2-(2-bromoethoxy)phenyl)-1H-indole (1.98 g, 100%). MS (M+H)+: 394/396/398.

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified

Sources & evidence

ORD record
ord-8cbddaf518034cadb0f62e4b923eea4d
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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