Triphenylphosphine → (5-Methylhexyl)(triphenyl)phosphanium bromide

HRID 1992250Notes

Reaction equation

HRID 1992250 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].[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].[CH3:7][CH:6]([CH3:8])[CH2:5][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 5207261-Bromo-5-methylhexane

Product 1

HCID 44126650(5-Methylhexyl)(triphenyl)phosphanium bromideYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 19 (2.30 g; 12.8 mmol) and triphenylphosphine (3.70 g; 14.1 mmol) was refluxed in toluene (12 mL) for 20 h. Then solvent was removed and the resulting crystal was washed with toluene (3 mL) and diethyl ether (3 mL) to give 4.57 g (10.4 mmol; 81% yield) of 10. m.p. 227-228° C.; 1H NMR (500 MHz, CD3CN) δ 0.82 (6H, d, J=6.6 Hz), 1.16 (2H, m), 1.42-1.52 (3H, m), 1.59 (2H, m), 3.30 (2H, m), 7.72 (12H, m), 7.85 (3H, m); 13C NMR (125 MHz, CD3CN) δ 22.7, 23.2, 28.4, 28.8, 28.9, 38.6, 131.2, 131.3, 134.7, 134.7, 136.0.

Workup

  1. customThen solvent was removed
  2. washthe resulting crystal was washed with toluene (3 mL) and diethyl ether (3 mL)

Sources & evidence

ORD record
ord-88f7e0f34a46467e932ef547d03e565c
Source dataset
uspto-grants-2010_01
Patent number
US07648972B2

Reaction notes

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