3,8-Phenanthroline → (3-Bromopropyl)triphenylphosphonium bromide

HRID 50461Notes

Reaction equation

HRID 50461 reaction equation
C1C2C(=CC=C3C=2C=CN=C3)C=NC=1.F[P-](F)(F)(F)(F)F.[Br:22][CH2:23][CH2:24][CH2:25][P+:26]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[Br-:22].[Br:22][CH2:23][CH2:24][CH2:25][P+:26]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 130646913,8-PhenanthrolineHCID 21301603(3-Bromopropyl)triphenylphosphonium hexafluorophosphate

Product 1

HCID 2723862(3-Bromopropyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Second, a mixture of 1.0 g (0.0056 mol) of 3,8-phenanthroline and 18.0 g (0.034 mol) of (3-bromopropyl)triphenylphosphonium hexafluorophosphate (obtained from the metathesis of (3-bromopropyl)triphenylphosphonium bromide with NaPF6) and 50 mL of DMF was heated under N2 to 95° C. overnight. After cooling to room temperature 150 mL of acetone was added to the reaction and a solid precipitated. This solid was isolated by vacuum filtration and then dissolved in a minimum amount of water. To this solution was added 1M aqueous NaBF4 until a precipitate formed. The solid was isolated by vacuum filtration and then recrystallized twice from ethanol and 1M aqueous NaBF4 and once from ethanol, acetonitrile and 1M aqueous NaBF4. Decolorization was achieved with charcoal during recrystallization. After drying under vacuum at 70° C. 4.1 g (65% yield) of an off-white solid was obtained.

Sources & evidence

ORD record
ord-b5b912f260a24e9186c996df8c4da5a1
Source dataset
uspto-grants-2004_03
Patent number
US06710906B2

Reaction notes

Loading…