Phosphine, triphenyl-, hydrobromide → (2,4-Dimethyl-5-methoxy-3-thenyl)triphenylphosphonium bromide

HRID 1764583Notes

Reaction equation

HRID 1764583 reaction equation
[CH3:1][C:2]1[S:3][C:4]([O:10][CH3:11])=[C:5]([CH3:9])[C:6]=1[CH2:7]O.[Br-:12].[C:13]1([PH+:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[Br-:12].[CH3:1][C:2]1[S:3][C:4]([O:10][CH3:11])=[C:5]([CH3:9])[C:6]=1[CH2:7][P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 517696Phosphine, triphenyl-, hydrobromideHCID 128752682,4-Dimethyl-3-hydroxymethyl-5-methoxythiophene

Product 1

HCID 86735242(2,4-Dimethyl-5-methoxy-3-thenyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6.1 G. (35.5 mmol) of 2,4-dimethyl-3-hydroxymethyl-5-methoxythiophene were added at 35° C. with vigorous stirring to a suspension of 13.4 g. (39.0 mmol) of triphenylphosphonium bromide in 250 ml. of acetonitrile. The deep purple color which was formed immediately, disappeared after some minutes. The reaction mixture was stirred for 3 hrs. The solvent was evaporated to a volume of about 25 ml. and an excess of cold ether was added. The solvent then was decanted from the resulting oily precipitate which was dissolved in warm acetone and again precipitated by adding cold ether. The solvent was decanted and the resulting oily residue was dried in high vacuum to yield (2,4-dimethyl-5-methoxy-3-thenyl)triphenylphosphonium bromide.

Workup

  1. customThe deep purple color which was formed immediately
  2. waitdisappeared after some minutes
  3. stirringThe reaction mixture was stirred for 3 hrs
  4. customThe solvent was evaporated to a volume of about 25 ml
  5. additionand an excess of cold ether was added
  6. customThe solvent then was decanted from the resulting oily precipitate which
  7. dissolutionwas dissolved in warm acetone
  8. customagain precipitated
  9. additionby adding cold ether
  10. customThe solvent was decanted
  11. customthe resulting oily residue was dried in high vacuum

Sources & evidence

ORD record
ord-2ccc6d9ed0bd4b70a7294187d4af1587
Source dataset
uspto-grants-1978_09
Patent number
US04116975

Reaction notes

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