Potassium Carbonate → Triphenylphosphine Oxide

HRID 2213977Notes

Reaction equation

HRID 2213977 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.BrCC1C=CC2C(=CC=CC=2)C=1.BrC1C=CC(C=[O:38])=CC=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CCCCCC>[C:14]1([P:7](=[O:38])([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 703202-BromomethylnaphthaleneHCID 707414-Bromobenzaldehyde

Product 1

HCID 13097Triphenylphosphine OxideYield 92%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

0.50 g (1.91 mmol) of triphenylphosphine, 0.42 g (1.90 mmol) of 2-bromomethylnaphthalene, 0.36 g (1.98 mmol) of p-bromobenzaldehyde, and 0.50 g (3.62 mmol) of K2CO3 were placed in a hardened-steel vial in a glove box under helium. The vial was sealed, and the sample was ball-milled for eight hours. The formed powder was first analyzed by solid state 31P{1H} CP MAS NMR spectroscopy, then loaded on a silica gel chromatography column, and the mixture of (E)- and (Z)-1-(p-bromophenyl)-2-(naphthyl)ethylenes (VII) (E:Z ratio ca. 3.5:1 by 1H NMR in CDCl3) was isolated in 93% yield, (0.54 g) by eluation with hexane and toluene. Triphenylphosphine oxide was further obtained from the same column in 92% yield (0.53 g) using a hexane-acetone mixture as an eluant. The separation and purification of the E-isomer was performed according to the previously described procedure (Brooks et al., J. Am. Chem. Soc. 121, 5444 (1999)) by the column chromatography on silica gel.

Workup

  1. customThe vial was sealed
  2. customthe sample was ball-milled for eight hours

Sources & evidence

ORD record
ord-1bb015fe32d449198f1ad39f3b4db800
Source dataset
uspto-grants-2006_09
Patent number
US07105714B2

Reaction notes

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