Water → Methyl 1-[3,5-Bis(trifluoromethyl)phenyl]cyclopropanecarboxylate

HRID 2047444Notes

Reaction equation

HRID 2047444 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[H-].[Na+].Br[CH2:23][CH2:24]Cl.O>CS(C)=O>[F:1][C:2]([F:18])([F:19])[C:3]1[CH:4]=[C:5]([C:13]2([C:14]([O:16][CH3:17])=[O:15])[CH2:24][CH2:23]2)[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 10401718Methyl 2-[3,5-bis(trifluoromethyl)phenyl]acetate

Product 1

HCID 21955134Methyl 1-[3,5-Bis(trifluoromethyl)phenyl]cyclopropanecarboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The compound (1.76 g) obtained in step 1 was dissolved in DMSO (30 mL), sodium hydride (0.59 g) was added at 0° C., and the mixture was stirred for 5 min. To the reaction mixture was added 2-bromo-1-chloroethane (0.77 mL), and the mixture was stirred at room temperature for 45 min. The reaction mixture was poured into water, and extracted twice with ethyl acetate. The extract was washed with saturated aqueous ammonium chloride solution, dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (10% ethyl acetate/hexane) to give methyl 1-[3,5-bis(trifluoromethyl)phenyl]cyclopropanecarboxylate (1.80 g, 94%).

Workup

  1. stirringthe mixture was stirred at room temperature for 45 min
  2. extractionextracted twice with ethyl acetate
  3. washThe extract was washed with saturated aqueous ammonium chloride solution
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated
  7. custompurified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2aab972e903a409d932a3c383875e270
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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