p-Toluenesulfonic acid → 1,1-Bis(2-fluoro-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethene

HRID 2165320Notes

Reaction equation

HRID 2165320 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[F:25])(O)[CH2:10][C:11]1[N:15]([CH3:16])[N:14]=[N:13][N:12]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)C>[F:25][C:19]1[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:18]=1[C:9]([C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[F:1])=[CH:10][C:11]1[N:15]([CH3:16])[N:14]=[N:13][N:12]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 147239921,1-Bis(2-fluoro-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanol

Product 1

HCID 147239931,1-Bis(2-fluoro-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethene

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A suspension of 1,1-bis(2-fluoro-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanol (7.3 g, 21.0 mmoles) in toluene (200 mL) with p-toluene sulfonic acid (3 g) and the mixture heated at reflux for 14 hours. After cooling, the mixture was diluted with diethyl ether and extracted with saturated sodium bicarbonate solution and water. The organic layer was dried (MgSO4) and evaporated. The residue was triturated with isopropyl ether to give the title compound; m.p.=58°-60° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 14 hours
  3. temperatureAfter cooling
  4. extractionextracted with saturated sodium bicarbonate solution and water
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated
  7. customThe residue was triturated with isopropyl ether

Sources & evidence

ORD record
ord-3f26c95392124eccb142b508caed6cbb
Source dataset
uspto-grants-1990_07
Patent number
US04939265

Reaction notes

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