Acetonitrile → (2,4-Dimethyl-3-thenyl)triphenylphosphonium bromide

HRID 1764587Notes

Reaction equation

HRID 1764587 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:9])[C:6]=1[CH2:7]O.[Br-:10].[C:11]1([PH+:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(#N)C>C(OCC)C>[Br-:10].[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:9])[C:6]=1[CH2:7][P+:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 517696Phosphine, triphenyl-, hydrobromideHCID 12875266(2,4-Dimethylthiophen-3-yl)methanol

Product 1

HCID 20285733(2,4-Dimethyl-3-thenyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4.4 G. of 2,4-dimethyl-3-hydroxymethylthiophene and 10.7 g. of triphenylphosphonium bromide were dissolved in 40 ml. of acetonitrile and stirred at 40° C. for 1 hour. The resulting solution was cooled and 150 ml. of ethyl ether was added. The white precipitate which formed was filtered and washed with cold acetone to yield (2,4-dimethyl-3-thenyl)triphenylphosphonium bromide, m.p. 262°-265° C.

Workup

  1. temperatureThe resulting solution was cooled
  2. customThe white precipitate which formed
  3. filtrationwas filtered
  4. washwashed with cold acetone

Sources & evidence

ORD record
ord-c7a7fe0014894cd1b888e8f07f4e12a1
Source dataset
uspto-grants-1978_09
Patent number
US04116975

Reaction notes

Loading…