Water → 4-Bromo-2-chloro-1-(ethylsulfanyl)benzene

HRID 70579

Reaction equation

HRID 70579 reaction equation
[CH2:1]([S-:3])[CH3:2].[Na+].[Br:5][C:6]1[CH:11]=[CH:10][C:9](F)=[C:8]([Cl:13])[CH:7]=1.O>CN(C)C=O>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([S:3][CH2:1][CH3:2])=[C:8]([Cl:13])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 35430654-Bromo-2-chloro-1-fluorobenzeneHCID 4459711Sodium ethanethiolate

Product 1

HCID 584523264-Bromo-2-chloro-1-(ethylsulfanyl)benzeneYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Sodium ethanethiolate (2.0 g) was added to a solution of 4-bromo-2-chloro-1-fluorobenzene (5.0 g) in N,N-dimethylformamide (20 mL), and the mixture was stirred at 65° C. for two hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:1→0:100) to give the title compound as a colorless oil (4.8 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:1→0:100)

Sources & evidence

ORD record
ord-a2e05521131d48fa887d2bc0d813faf0
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Linked notes

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