Bromine → HCID 57517493, compound

HRID 2368095Notes

Reaction equation

HRID 2368095 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH3:10].[S-:11][C:12]#[N:13].[K+].BrBr.C(=O)([O-])O.[Na+]>C(O)(=O)C>[F:1][C:2]1[C:3]([O:9][CH3:10])=[CH:4][C:5]2[N:6]=[C:12]([NH2:13])[S:11][C:7]=2[CH:8]=1

Participants

6

Reactant 4

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 516892Sodium BicarbonateHCID 27745334-Fluoro-3-methoxyaniline

Product 1

HCID 57517493HCID 57517493, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A suspension of 4-fluoro-3-methoxyaniline (1.00 g) and potassium thiocyanate (2.07 g) in acetic acid (20 mL) was stirred at room temperature for 20 min, and a solution of bromine (0.380 mL) in acetic acid (1 mL) was added thereto over 5 min. The reaction mixture was stirred at room temperature for 30 min, neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (670 mg).

Workup

  1. waitover 5 min
  2. stirringThe reaction mixture was stirred at room temperature for 30 min
  3. extractionextracted with ethyl acetate
  4. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-549e21adc75d4aa89fa5c9bc1180cd5b
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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