1,3-Dibromopropane → (3-Bromopropyl)triphenylphosphonium bromide

HRID 2247133Notes

Reaction equation

HRID 2247133 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][CH2:22][CH2:23]Br>C1(C)C=CC=CC=1>[Br-:20].[Br:20][CH2:21][CH2:22][CH2:23][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 80011,3-DibromopropaneHCID 11776Triphenylphosphine

Product 1

HCID 2723862(3-Bromopropyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of triphenylphosphine (511 g, 1.85 mol; assay: 95.0%) in toluene (800 g), 1,3-dibromopropane (371 g, 1.82 mol; assay: 99.0%) was added slowly within 1 hour at <5° C. After complete addition the solution was heated to reflux for 17 hours whereupon a suspension was obtained which was then cooled to room temperature. The product was filtered off at 20° C., washed with toluene (2×800 g) and dried under vacuum (21 h, 60° C.) to give 3-bromopropyltriphenylphosphonium bromide (Olo-IM3) as a white, crystalline solid (yield: 757 g, 1.63 mol, 89.6%).

Workup

  1. additionAfter complete addition the solution
  2. temperaturewas heated
  3. temperatureto reflux for 17 hours whereupon a suspension
  4. customwas obtained which
  5. filtrationThe product was filtered off at 20° C.
  6. washwashed with toluene (2×800 g)
  7. customdried under vacuum (21 h, 60° C.)

Sources & evidence

ORD record
ord-6aa2876cbd784f77b6dbdc8f115f0ae2
Source dataset
uspto-grants-2010_03
Patent number
US07687646B2

Reaction notes

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