Triphenylphosphine → Furo[3,2-c]pyridin-2-ylmethyltriphenylphosphonium bromide hydrochloride

HRID 217164Notes

Reaction equation

HRID 217164 reaction equation
[ClH:1].[Br:2][CH2:3][C:4]1[O:12][C:11]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[CH:5]=1.[CH:13]1[CH:18]=[CH:17][C:16]([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1>C1COCC1.CCO>[ClH:1].[Br-:2].[O:12]1[C:11]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[CH:5]=[C:4]1[CH2:3][P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:16]1[CH:15]=[CH:14][CH:13]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 68939591Furo[3,2-c]pyridine,2-(bromomethyl)-,hydrochloride

Product 1

HCID 86629541Furo[3,2-c]pyridin-2-ylmethyltriphenylphosphonium bromide hydrochloride

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of 2-bromomethylfuro[3,2-c]pyridine hydrochloride (Preparation 5, 2.12 g, 8.5 mmol) and PPh3 (2.24 g, 8.5 mmol) in anhydrous THF-EtOH (1:1, 80 mL) was heated under reflux for 3 d. The solvents were removed under reduced pressure, then the residual solid was triturated with hot THF to furnish the title compound: RT=2.32 min.

Workup

  1. temperatureunder reflux for 3 d
  2. customThe solvents were removed under reduced pressure
  3. customthe residual solid was triturated with hot THF

Sources & evidence

ORD record
ord-34f05c75e491479cad1c39335ca59071
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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