3-Fluoroaniline → 4-Amino-2-fluorophenyl thiocyanate

HRID 412485Notes

Reaction equation

HRID 412485 reaction equation
BrN1C(=O)CCC1=O.[S-:9][C:10]#[N:11].[K+].[F:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>CO>[F:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[S:9][C:10]#[N:11])[NH2:17]

Participants

5

Reactant 3

HCID 97423-FluoroanilineHCID 67184N-bromobutanimideHCID 516872Potassium thiocyanate

Product 1

HCID 222450794-Amino-2-fluorophenyl thiocyanate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

N-Bromosuccinimide (1.76 g, 9.89 mmol) and potassium thiocyanate (1.75 g, 18.0 mmol) in methanol (30 ml) were stirred for 15 minutes at room temperature. The reaction mixture was cooled to 0° C., and 3-fluoroaniline (1.00 g, 9.0 mmol) was added dropwise. The mixture was stirred at 0° C. for 2 h. Solvent was removed under vacuum, and the residue was washed with dichloromethane. The mixture was filtered to remove succinimide by-product, and the solution was washed with water, brine, and dried (MgSO4). Solvent was removed under vacuum to afford the desired product as a colorless oil. Yield 1.45 g (96%). 1H NMR.

Workup

  1. customSolvent was removed under vacuum
  2. washthe residue was washed with dichloromethane
  3. filtrationThe mixture was filtered
  4. customto remove succinimide by-product
  5. washthe solution was washed with water, brine
  6. dry with materialdried (MgSO4)
  7. customSolvent was removed under vacuum

Sources & evidence

ORD record
ord-0412ebc0ca3f4c9c8e682af7ba4d1677
Source dataset
uspto-grants-2003_05
Patent number
US06562844B2

Reaction notes

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