Butyl bromide → Tri-n-octyl-n-butylphosphonium bromide

HRID 614579Notes

Reaction equation

HRID 614579 reaction equation
[CH2:1]([P:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Br:26][CH2:27][CH2:28][CH2:29][CH3:30]>>[Br-:26].[CH2:18]([P+:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

3

Reactant 2

HCID 8002Butyl bromideHCID 20851Trioctylphosphine

Product 1

HCID 22731140Tri-n-octyl-n-butylphosphonium bromide

Procedure

Tri-n-octyl-n-butylphosphonium bromide is prepared by slowly dripping tri-(n-octyl)phosphine (740 grams) into refluxing 1-bromobutane (500 grams) in a nitrogen atmosphere. Reflux is continued one hour after final addition then the solution is cooled with stirring for about 18 hours, followed by vacuum removal of excess 1-bromobutane at 60° C. This product, 1210 grams from two successive preparations, is added to 880 grams of sodium 3,5-dicarbomethoxybenzenesulfonate in 2500 milliliters of water and stirred for at least 1 hour at 85° C. then the heat is removed and the oil in water mixture is allowed to stir and cool for about 18 hours. The oil layer is separated from the water, rinsed with 1000 milliliters of water and dried at about 80° C. at a pressure less than 2 torr for 18 hours. This product, an oil, is tri-n-octyl-n-butylphosphonium 3,5-dicarbomethoxybenzenesulfonate with 4.2% phosphorous and 4.7% sulfur by analysis.

Workup

  1. temperatureReflux
  2. additionafter final addition
  3. temperaturethe solution is cooled
  4. customfollowed by vacuum removal of excess 1-bromobutane at 60° C
  5. additionThis product, 1210 grams from two successive preparations, is added to 880 grams of sodium 3,5-dicarbomethoxybenzenesulfonate in 2500 milliliters of water
  6. stirringstirred for at least 1 hour at 85° C.
  7. customthe heat is removed
  8. stirringto stir
  9. temperaturecool for about 18 hours
  10. customThe oil layer is separated from the water
  11. washrinsed with 1000 milliliters of water
  12. customdried at about 80° C. at a pressure less than 2 torr for 18 hours

Sources & evidence

ORD record
ord-f8457854e68845988c030212b48859ea
Source dataset
uspto-grants-1979_03
Patent number
US04145473

Reaction notes

Loading…