Triphenylphosphine → Phosphonium, [3-(methoxymethoxy)propyl]triphenyl-, bromide

HRID 493902

Reaction equation

HRID 493902 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH3:8].[C:9]1([P:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[Br-:1].[CH3:8][O:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][P+:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 127092881-Bromo-3-methoxymethoxypropane

Product 1

HCID 11178287Phosphonium, [3-(methoxymethoxy)propyl]triphenyl-, bromide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-bromo-3-(methoxymethoxy)propane (0.46 g, 2.5 mmol) in anhydrous toluene (1.5 mL) was added triphenylphoshine (0.71 g, 2.7 mmol) under argon with stirring. The mixture was heated at 100° C. for 20 h and cooled to room temperature. The liquid was decanted and the solid residue was grounded with spatula, filtered and washed several times with ether. After drying overnight in vacuum dessicator colorless crystals of phosphonium salt A (0.98 g, 88%) could be used in the Wittig reaction without further purification.

Workup

  1. temperaturecooled to room temperature
  2. customThe liquid was decanted
  3. filtrationfiltered
  4. washwashed several times with ether
  5. dry with materialAfter drying overnight in vacuum dessicator colorless crystals of phosphonium salt A (0.98 g, 88%)
  6. customcould be used in the Wittig reaction without further purification

Sources & evidence

ORD record
ord-1099846e47874159896379355ca06fd9
Source dataset
uspto-grants-2009_05
Patent number
US07538098B2

Linked notes

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