Chlorotrimethylsilane → HCID 21808417, compound

HRID 861253Notes

Reaction equation

HRID 861253 reaction equation
[C:1]([C:3]1[C:4]([C:20]([F:23])([F:22])[F:21])=[N:5][N:6]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=2[Cl:19])[CH:7]=1)#[N:2].C([Li])CCC.[CH3:29][Si:30](Cl)([CH3:32])[CH3:31]>O1CCCC1.ClCCl>[C:1]([C:3]1[C:4]([C:20]([F:23])([F:21])[F:22])=[N:5][N:6]([C:8]2[C:9]([Cl:19])=[CH:10][C:11]([C:15]([F:17])([F:18])[F:16])=[CH:12][C:13]=2[Cl:14])[C:7]=1[Si:30]([CH3:32])([CH3:31])[CH3:29])#[N:2]

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 14280195HCID 14280195, compoundHCID 178418339Butyllithium

Product 1

HCID 21808417HCID 21808417, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of 4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-trifluoromethylpyrazole (1.5 g) in dry tetrahydrofuran cooled to -78° C. was treated with a solution of n-butyl lithium (2.6M in hexane, 1.71 ml) dropwise under nitrogen. The temperature was kept below -65° C. during the addition, and the resultant solution kept at -78° C. for 1 hour. A solution of trimethylsilyl chloride (0.56 ml) in dry tetrahydrofuran (2 ml) was then added, dropwise, during 2 minutes. The mixture was allowed to reach room temperature over 2 hours, left overnight and evaporated in vacuo to give a pale yellow solid. This was dissolved in dichloromethane, washed with water, dried over anhydrous magnesium sulphate, and evaporated in vacuo. The product was recrystallized from hexane to give 4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-trifluoromethyl-5-trimethylsilylpyrazole as white crystals, m.p. 108°-110° C.

Workup

  1. additionThe temperature was kept below -65° C. during the addition
  2. waitto reach room temperature over 2 hours
  3. waitleft overnight
  4. customevaporated in vacuo
  5. customto give a pale yellow solid
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated in vacuo
  9. customThe product was recrystallized from hexane

Sources & evidence

ORD record
ord-19cf424e1d444d16bc03353513cd4978
Source dataset
uspto-grants-1998_02
Patent number
US05714191

Reaction notes

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