Triphenylphosphonium bromide → Triphenylphosphine

HRID 1021074Notes

Reaction equation

HRID 1021074 reaction equation
Br.[C:2]1([P:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[C:15]1([P:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 1

HCID 80811Triphenylphosphonium bromide

Product 1

HCID 11776Triphenylphosphine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of triphenylphosphine hydrobromide (22.0 g, 64.0 mmol) in MeOH (80 mL) was added a solution of alcohol 2 (8.72 g, 64.0 mmol) in MeOH (70 mL) and the reaction mixture was stirred at room temperature for 48 h. The reaction solution was concentrated under reduced pressure and the residue was triturated with a mixture of acetone (20 mL) and diethyl ether (50 mL). The precipitate was collected by vacuum filtration, washed with diethyl ether (30 mL) and hexanes (30 mL), and concentrated under reduced pressure to provide triphenylphosphine salt 3 as a white solid. Yield (23.0 g, 78%): mp 240-246° C. 1H NMR (300 MHz, DMSO-d6) δ 7.51-7.95 (m, 15H), 7.15 (dt, J=7.7, 2.6 Hz, 1H), 6.96 (d, J=7.7 Hz, 2H), 4.94 (d, J=14.6 Hz, 2H), 1.76 (s, 6H); ESI MS m/z 381 [M−Br]+; HPLC (Method 1) 97.0% (AUC), tR=13.78 min.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was triturated with a mixture of acetone (20 mL) and diethyl ether (50 mL)
  3. filtrationThe precipitate was collected by vacuum filtration
  4. washwashed with diethyl ether (30 mL) and hexanes (30 mL)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c9032d8821a14fbc899a2003198d83ca
Source dataset
uspto-grants-2014_05
Patent number
US08716529B2

Reaction notes

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