Chlorotrimethylsilane → 5-Fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester

HRID 2069257Notes

Reaction equation

HRID 2069257 reaction equation
[F:1][C:2]1[C:3]([C:14]([F:17])([F:16])[F:15])=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:18][Si](C)(C)Cl>CO>[CH3:18][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([F:1])[C:3]([C:14]([F:15])([F:16])[F:17])=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 6397Chlorotrimethylsilane2×HCID 589645095-Fluoro-2-nitro-4-trifluoromethyl-benzoic acid

Product 1

HCID 589644905-Fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6.2 g (24.5 mmole) of 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid in 250 ml of methanol is treated with 9.28 ml (73.5 mmole) of trimethylchlorosilane and heated to reflux for six days during which every evening additional 9.28 ml of trimethylchlorosilane are added. The cooled solution is evaporated in vacuo and distributed between dichloro-methane and water. The combined organic phases are extracted twice with 50 ml of a 0.5 M sodium hydroxide solution and with 50 ml brine. After drying over sodium sulfate, filtering and evaporation the crystalline residue is recrystallized from acetone/petrolether to give 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester of m.p. 66-68° C.

Workup

  1. temperatureheated
  2. additionare added
  3. customThe cooled solution is evaporated in vacuo
  4. extractionThe combined organic phases are extracted twice with 50 ml of a 0.5 M sodium hydroxide solution and with 50 ml brine
  5. dry with materialAfter drying over sodium sulfate
  6. filtrationfiltering
  7. customevaporation the crystalline residue
  8. customis recrystallized from acetone/petrolether

Sources & evidence

ORD record
ord-614acde52a084436a71049aae0fe78f6
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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