Methanol → Phosphonium, (bromomethyl)triphenyl-, bromide (1:1)

HRID 399111

Reaction equation

HRID 399111 reaction equation
[Br-:1].[C:2]1([PH+:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:22].[CH3:25]O>C1C=CC=CC=1>[Br-:22].[Br:1][CH2:25][P+:8]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24614Phosphorus tribromideHCID 517696Phosphine, triphenyl-, hydrobromide

Product 1

HCID 2733422Phosphonium, (bromomethyl)triphenyl-, bromide (1:1)

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of hydroxymethyl)triphenylphosphonium bromide and phosphorus tribromide in benzene is heated at reflux for 23 h with stirring. After this time the solution is dark orange and an orange solid is present. The mixture is cooled to 25° C. and methanol is added. The solvent was removed at reduced pressure and the residue treated with water to extract the phosphonium salt. The aqueous extracts were saturated with solid potassium bromide and extracted with chloroform. The phosphonium salts are crystallized from hot chloroform by addition of ethyl acetate.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 23 h
  3. customThe solvent was removed at reduced pressure
  4. additionthe residue treated with water
  5. extractionto extract the phosphonium salt
  6. extractionextracted with chloroform
  7. customThe phosphonium salts are crystallized from hot chloroform by addition of ethyl acetate

Sources & evidence

ORD record
ord-7237fbfbfe244ea4b5590452eb3af00b
Source dataset
uspto-grants-1998_10
Patent number
US05817776

Linked notes

Loading…