Triphenylphosphine → Phosphonium, [(4-methoxy-3-nitrophenyl)methyl]triphenyl-, bromide

HRID 1883261Notes

Reaction equation

HRID 1883261 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH2:7][Br:8])([O-:3])=[O:2].[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[Br-:8].[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:6]([CH2:7][P+:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 115796484-(Bromomethyl)-1-methoxy-2-nitrobenzene

Product 1

HCID 11237519Phosphonium, [(4-methoxy-3-nitrophenyl)methyl]triphenyl-, bromideYield 88.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

3-Nitro-4-methoxybenzyl bromide (3, 119 g) is charged into 1000 ml of stirred toluene in a 2 litre three-necked flask equipped with a mechanical stirrer, a thermometer, a T piece, a funnel for the addition of solids and a reflux condenser surmounted by a bubble counter, and the stirred mixture, warmed to 25° C., forms a solution. Triphenylphosphine (126.5 g) is then added and the resultant solution is gradually heated to 60° C.; a precipitate begins to form at about 30° C. The mixture is maintained at 60-65° C. for 4 hours, is then cooled to 30° C. and is filtered through a sintered glass filter. The filter cake is washed on the filter twice with 300 ml portions of toluene, sucked dry and dried in an oven (35° C./20 mmHg/ hours). (4-Methoxy-3-nitrobenzyl)triphenylphosphonium bromide (217 g) is obtained with a chemical yield of 88%. The synthesis is also described in the publication: (solvent used: dichloromethane) K. G. Piney et al., Bioorg. Med. Chem., 8(2000), 2417-2425.

Workup

  1. customequipped with a mechanical stirrer
  2. additiona thermometer, a T piece, a funnel for the addition of solids and a reflux condenser
  3. customto form at about 30° C
  4. temperatureThe mixture is maintained at 60-65° C. for 4 hours
  5. temperatureis then cooled to 30° C.
  6. filtrationis filtered through a sintered glass
  7. filtrationfilter
  8. washThe filter cake is washed on the
  9. filtrationfilter twice with 300 ml portions of toluene
  10. customsucked dry
  11. customdried in an oven (35° C./20 mmHg/ hours)

Sources & evidence

ORD record
ord-4d430b026bfe44229be2bbd2797eff6f
Source dataset
uspto-grants-2004_07
Patent number
US06759555B2

Reaction notes

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