2-Fluoroaniline → 544662-80-8

HRID 932227Notes

Reaction equation

HRID 932227 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[F:7][C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10]>C(Cl)Cl.N1C=CC=CC=1.CCOC(C)=O>[F:7][C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH:10][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4]

Participants

6

Reactant 2

HCID 95842-FluoroanilineHCID 11667Ethanesulfonyl chloride

Product 1

HCID 4693938544662-80-8

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethanesulfonyl chloride (0.368 ml, 3.89 mmol) in DCM (1 ml) and pyridine (1 ml) was added 2-fluoroaniline (0.360 ml, 3.89 mmol) at rt and the reaction was stirred at 50° C. for 5 hours. The reaction was then stirred at rt overnight. The reaction was diluted with EtOAc and washed with H2O and sat. NaCl solution. The organic layer was dried over Na2SO4 and concentrated. Purification of the residue by flash chromatography on silica gel (eluent: 0% to 35% EtOAc/hexane) provided the title compound as a white solid.

Workup

  1. stirringThe reaction was then stirred at rt overnight
  2. washwashed with H2O and sat. NaCl solution
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customPurification of the residue by flash chromatography on silica gel (eluent: 0% to 35% EtOAc/hexane)

Sources & evidence

ORD record
ord-14ecb425d14c4641893dbcdac1ff90e2
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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