Acifluorfen → HCID 13218899, compound

HRID 1979616Notes

Reaction equation

HRID 1979616 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11].N1(C2CCCCCCCCCC2)CCCCCCCCCN1.Cl[CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50]>CS(C)=O>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([O:12][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])=[O:11]

Participants

5

Reactant 3

HCID 44073AcifluorfenHCID 75361Silane, (chloromethyl)trimethyl-HCID 57346892Diazabicycloundecane

Product 1

HCID 13218899HCID 13218899, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

18.1 g (0.05 mol) of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitro-benzoic acid are dissolved in 100 ml of dimethylsulphoxide. 9.8 g of diazabicycloundecane are added at 20° C., while cooling. The mixture is stirred for a further half hour. 7.4 g (0.06 mol) of chloromethyl-trimethylsilane are then added dropwise at 20° C., and the mixture is heated at 100° C. for 20 hours. The reaction mixture is thereafter concentrated, and the residue is taken up in toluene. The organic phase is washed successively with dilute hydrochloric acid, aqueous sodium hydroxide solution and water, and is then dried and evaporated down. The residue is dissolved in ligroin, the solution is stirred under active charcoal, the latter is filtered off under suction over kieselguhr, and the filtrate is then concentrated. 20 g (89% of theory) of trimethyl-silyl-methyl 5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoate are obtained as a viscous oil.

Workup

  1. temperaturewhile cooling
  2. concentrationThe reaction mixture is thereafter concentrated
  3. washThe organic phase is washed successively with dilute hydrochloric acid, aqueous sodium hydroxide solution and water
  4. customis then dried
  5. customevaporated down
  6. dissolutionThe residue is dissolved in ligroin
  7. stirringthe solution is stirred under active charcoal
  8. filtrationthe latter is filtered off under suction over kieselguhr
  9. concentrationthe filtrate is then concentrated

Sources & evidence

ORD record
ord-7b8eb5676d8c4729b2d3ee209f6d0af9
Source dataset
uspto-grants-1984_11
Patent number
US04481365

Reaction notes

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