2-Fluoro-5-(trifluoromethyl)aniline → 3-Ethoxythiocarbonylthio-4-fluorobenzotrifluoride

HRID 49955

Reaction equation

HRID 49955 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:3]=1N.N([O-])=O.[Na+].[C:17](=[S:22])([O:19][CH2:20][CH3:21])[S-:18].[K+]>O.Cl>[CH2:20]([O:19][C:17]([S:22][C:3]1[CH:5]=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:7]=[CH:8][C:2]=1[F:1])=[S:18])[CH3:21]

Participants

6

Reactant 3

HCID 1363492-Fluoro-5-(trifluoromethyl)anilineHCID 2735045Potassium ethylxanthateHCID 23668193Sodium Nitrite

Product 1

HCID 120973533-Ethoxythiocarbonylthio-4-fluorobenzotrifluorideYield 99%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Conditions

Temperature
-59 °C

Procedure

2-Fluoro-5-trifluoromethylaniline (14 g) was suspended in 30 ml of water and 10 ml of concentrated hydrochloric acid. The suspension was cooled to −5° C. while a solution of 5.93 g of sodium nitrite in 30 ml of water was added dropwise, followed by stirring at −59° C. for 2 hours. Then the solution was added to a solution of 16 g of potassium O-ethyl dithiocarbonate in 20 ml of water (40 to 50° C.), followed by stirring for 1 hour. The reaction mixture was extracted with an aqueous solution of ethyl acetate, dried and concentrated, giving 22 g of 3-ethoxythiocarbonylthio-4-fluorobenzotrifluoride.

Workup

  1. additionwas added dropwise
  2. stirringby stirring for 1 hour
  3. extractionThe reaction mixture was extracted with an aqueous solution of ethyl acetate
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0f9fecd1643e4add9ad5763b945bc4a1
Source dataset
uspto-grants-2004_03
Patent number
US06710062B1

Linked notes

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