Triphenylphosphine → Phosphonium, (6-hydroxyhexyl)triphenyl-, bromide

HRID 921510Notes

Reaction equation

HRID 921510 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Br: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>C(#N)C>[Br-:8].[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][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 779706-Bromo-1-hexanol

Product 1

HCID 2784664Phosphonium, (6-hydroxyhexyl)triphenyl-, bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-hydroxyhexyl bromide (10.36 g, 0.057 mol) and triphenylphosphine (5 g, 0.019 mol) in 100 ml of acetonitrile was refluxed for 2 days. After removal of the solvent, the residue was washed three times with ether. The solid was purified by silica chromatography using heptane/ethyl acetate and methylene chloride/MeOH as eluent to give viscous pale white material.

Workup

  1. temperaturewas refluxed for 2 days
  2. customAfter removal of the solvent
  3. washthe residue was washed three times with ether
  4. customThe solid was purified by silica chromatography
  5. customto give viscous pale white material

Sources & evidence

ORD record
ord-295be3426c694685be64bf58c214f5c6
Source dataset
uspto-grants-2016_03
Patent number
US09273343B2

Reaction notes

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