Hydrogen Bromide → Phosphine, triphenyl-, hydrobromide

HRID 256415Notes

Reaction equation

HRID 256415 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.[BrH:20].C(OCC)C>C1(C)C=CC=CC=1>[Br-:20].[C:14]1([PH+:7]([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

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 11776Triphenylphosphine

Product 1

HCID 517696Phosphine, triphenyl-, hydrobromideYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 26.23 g (0.10 mole) triphenylphosphine in 100 ml toluene at 0°-5° C. was perfused with HBr gas for 20 minutes, 250 ml ethyl ether was added and the mixture stirred for 20 minutes. The mixture was filtered, the white solid cake slurried in ether (500 ml), filtered again and air-dried to obtain 33.2 g (97%) of triphenylphosphonium bromide, m.p. 203°-205° C. (decomp.). In a separate flask 33 g (0.096 mole) of this salt, 11.9 g (0.096 mole) o-hydroxybenzyl alcohol and 100 ml dry acetonitrile were combined and heated at reflux for two hours. The resulting solution was cooled, filtered, the cake washed with 100 ml acetonitrile and dried in vacuo at 120° C. to obtain 26.2 g (61%) of the desired product, m.p. 223°-225° C. Mass spectrum (m/e): 368, 291, 262, 107.

Workup

  1. filtrationThe mixture was filtered
  2. filtrationfiltered again
  3. customair-dried

Sources & evidence

ORD record
ord-5ca9c12179f747729d6cfe74d56c10fe
Source dataset
uspto-grants-1987_10
Patent number
US04703052

Reaction notes

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