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

HRID 1992251Notes

Reaction equation

HRID 1992251 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 20 (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-563c7ca96c51483481d03622a02bfb68
Source dataset
uspto-grants-2010_01
Patent number
US07648973B2

Reaction notes

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