Triphenylphosphine → [2-(1,3-Dioxolan-2-yl)propan-1-yl]triphenylphosphonium bromide

HRID 1728992Notes

Reaction equation

HRID 1728992 reaction equation
[Br:1][CH2:2][CH:3]([CH:5]1[O:9][CH2:8][CH2:7][O:6]1)[CH3:4].[C:10]1([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C=CC=CC=1>[Br-:1].[O:6]1[CH2:7][CH2:8][O:9][CH:5]1[CH:3]([CH3:4])[CH2:2][P+:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 143837522-(1-Bromopropan-2-yl)-1,3-dioxolane

Product 1

HCID 19016931[2-(1,3-Dioxolan-2-yl)propan-1-yl]triphenylphosphonium bromideYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 110 g (0.56 mol) of 2-(1-bromopropan-2-yl)-1,3-dioxolane, 148.5 g (0.56 mol) of triphenylphosphine and 550 ml of anhydrous toluene is heated at reflux under nitrogen for 24 h. The paste-like salt phase is separated and washed with 5×200 ml of anhydrous ethyl ether. After drying under vacuum there are obtained 191 g of [2-(1,3-dioxolan-2-yl)propan-1-yl]triphenylphosphonium bromide (white solid; yield 75%).

Workup

  1. temperatureis heated
  2. temperatureat reflux under nitrogen for 24 h
  3. customThe paste-like salt phase is separated
  4. washwashed with 5×200 ml of anhydrous ethyl ether
  5. customAfter drying under vacuum

Sources & evidence

ORD record
ord-1ae9a213ae5042909fa1d1e18d5bf2e6
Source dataset
uspto-grants-1994_07
Patent number
US05329052

Reaction notes

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