Ethylene Glycol → 1-(4-[(Trifluoromethyl)thio]phenyl}cyclopropanecarboxylic acid

HRID 504333Notes

Reaction equation

HRID 504333 reaction equation
[F:1][C:2]([F:14])([F:13])[S:3][C:4]1[CH:9]=[CH:8][C:7](CC#N)=[CH:6][CH:5]=1.Br[CH2:16][CH2:17]Cl.[OH-:19].[Na+].O.[CH2:22]([OH:25])[CH2:23]O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[F:14][C:2]([F:1])([F:13])[S:3][C:4]1[CH:5]=[CH:6][C:7]([C:23]2([C:22]([OH:25])=[O:19])[CH2:17][CH2:16]2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 78491-Bromo-2-ChloroethaneHCID 27779054-(Trifluoromethylthio)phenylacetonitrileHCID 23719242Sodium hydroxide--water (1/1/1)

Product 1

HCID 666622041-(4-[(Trifluoromethyl)thio]phenyl}cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of {4-[(trifluoromethyl)thio]phenyl}acetonitrile (1.15 g, 0.00529 mol), 1-bromo-2-chloro-ethane, (880 μL, 0.010 mol), benzyltriethyl ammonium chloride (70 mg, 0.0003 mol) and 1.5 ml of 50% NaOH-water (w/w) solution was kept at 50° C. with stirring for 3 hours. LCMS data supported that the reaction was complete. To the above solution 1,2-ethanediol (10 mL, 0.2 mol) was added. The mixture was heated at 100° C. overnight. After work-up 1.2 g of solid product was obtained. LC/MS: 387.1 (M+H+).

Workup

  1. customwas kept at 50° C.

Sources & evidence

ORD record
ord-39955b1ef10f4c40a1f382ac516f570e
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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