2-Methylthiophene → Triphenyl(2-thienylmethyl)phosphonium Bromide

HRID 986423Notes

Reaction equation

HRID 986423 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[Br:7]N1C(=O)CCC1=O.BrCC1SC=CC=1.[C:22]1([P:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)(Cl)(Cl)Cl.O1CCCC1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br-:7].[S:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[CH2:1][P+:28]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 111262-MethylthiopheneHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 118299782-(Bromomethyl)thiophene

Product 1

HCID 10741697Triphenyl(2-thienylmethyl)phosphonium BromideYield 724.2%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-methylthiophene (10 g, 0.10 mol) and N-bromosuccinimide (18 g, 0.10 mol) in carbon tetrachloride (100 ml) was heated to reflux under nitrogen. Benzoyl peroxide (50 mg) was added and the mixture was refluxed for 3 hours. After cooling to room temperature the reaction was filtered and concentrated to a dark oil. The crude 2-bromomethylthiophene and triphenylphosphine (29 g, 0.011 mol) were dissolved in tetrahydrofuran (170 ml) under nitrogen and heated to reflux for 4 hours and then cooled to room temperature for precipitation. The product was collected by filtration, washed with ethyl ether (4×15 ml) and dried to afford (2-thienyl)methyl triphenylphosphonium bromide (35 g, 80%). m.p. 250° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen
  3. temperaturethe mixture was refluxed for 3 hours
  4. filtrationwas filtered
  5. concentrationconcentrated to a dark oil
  6. temperatureheated
  7. temperatureto reflux for 4 hours
  8. temperaturecooled to room temperature for precipitation
  9. filtrationThe product was collected by filtration
  10. washwashed with ethyl ether (4×15 ml)
  11. customdried

Sources & evidence

ORD record
ord-d2f30e79721a46b6b6687a3768bf2e95
Source dataset
uspto-grants-1987_12
Patent number
US04713393

Reaction notes

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