Methyl iodide → HCID 15075816, compound

HRID 322819Notes

Reaction equation

HRID 322819 reaction equation
[CH2:1]([Li])CCC.C(NC(C)C)(C)C.[F:13][C:14]1[C:22]([CH3:23])=[C:21]([F:24])[C:20]([F:25])=[CH:19][C:15]=1[C:16]([OH:18])=[O:17].CI>O1CCCC1.O.C(OCC)C.CCCCCC>[F:13][C:14]1[C:22]([CH3:23])=[C:21]([F:24])[C:20]([F:25])=[C:19]([CH3:1])[C:15]=1[C:16]([OH:18])=[O:17]

Participants

9

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 118055142,4,5-Trifluoro-3-methylbenzoic acidHCID 178418339Butyllithium

Product 1

HCID 15075816HCID 15075816, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

70 ml of 1.69M n-hexane solution of n-butyllithium was added dropwise to solution of 18 ml of diisopropylamine in 75 ml of tetrahydrofuran at −65 ° C. under nitrogen stream, and the mixture was stirred at the same temperature for 15 minutes. To the solution was added dropwise solution of 9.5 g of 2,4,5-trifluoro-3-methylbenzoic acid in 75 ml of tetrahydrofuran at −60° C., and the mixture was stirred at the same temperature for 15 minutes. To the solution was added dropwise 9.5 ml of methyl iodide at −70° C., and the mixture was stirred at the same temperature for 30 minutes and overnight at room temperature. Diethylether and water were added for separation, and the aqueous layer was collected. The aqueous layer was acidified by adding conc. hydrochloric acid, and extracted with diethylether. The organic layer was dried over ahnydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 6.6 g of the title compound.

Workup

  1. stirringthe mixture was stirred at the same temperature for 15 minutes
  2. stirringthe mixture was stirred at the same temperature for 30 minutes and overnight at room temperature
  3. customthe aqueous layer was collected
  4. additionby adding conc. hydrochloric acid
  5. extractionextracted with diethylether
  6. dry with materialThe organic layer was dried over ahnydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-aa47486cbb044de4aeddc45660e88025
Source dataset
uspto-grants-2001_04
Patent number
US06211375B1

Reaction notes

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