Sodium Iodide → 1-Chloro-4-fluoro-2-(isothiocyanatomethyl)benzene

HRID 524121Notes

Reaction equation

HRID 524121 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[Cl:10].[Na+].[I-].[C:13]([S-:15])#[N:14].[K+]>CN(C=O)C.O>[Cl:10][C:4]1[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:3]=1[CH2:2][N:14]=[C:13]=[S:15]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 516872Potassium thiocyanateHCID 27736232-Chloro-5-fluorobenzyl bromide

Product 1

HCID 866548531-Chloro-4-fluoro-2-(isothiocyanatomethyl)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(bromomethyl)-1-chloro-4-fluorobenzene (25, 22.3 g, 100 mmol) in dry DMF (150 mL) were added NaI (16.0 g, 107 mmol) and KSCN (19.5 g, 200 mmol) The mixture was heated under N2 at 90° C. for 18 h. After cooling to RT, the mixture was diluted with water (200 mL), and extracted with EtOAc (200 mL×2). The combined extracts were washed with brine, dried over MgSO4, and concentrated to give crude product. This was purified by column chromatography on silica gel, and eluted with petroleum ether to provide 1-chloro-4-fluoro-2-(isothiocyanatomethyl)benzene (26).

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with EtOAc (200 mL×2)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give crude product
  7. customThis was purified by column chromatography on silica gel
  8. washeluted with petroleum ether

Sources & evidence

ORD record
ord-efe09d20fb1e49e1ab822e171b8b9b7d
Source dataset
uspto-grants-2016_05
Patent number
US09340523B2

Reaction notes

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