Chlorosuccinimide → 2-Chloro-4-(difluoromethoxy)aniline(WXFC0705)

HRID 2205908Notes

Reaction equation

HRID 2205908 reaction equation
[Cl:1]N1C(=O)CCC1=O.[F:9][CH:10]([F:19])[O:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>C(#N)C>[Cl:1][C:17]1[CH:18]=[C:12]([O:11][CH:10]([F:19])[F:9])[CH:13]=[CH:14][C:15]=1[NH2:16]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 7373634-(Difluoromethoxy)aniline

Product 1

HCID 545952502-Chloro-4-(difluoromethoxy)aniline(WXFC0705)Yield 53.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Chlorosuccinimide (0.84 g, 6.28 mmol) was added to a solution of 4-(difluoromethoxy)aniline (1 g, 6.28 mmol) in acetonitrile (10 ml). The reaction was refluxed for 3 hours and then cooled to room temperature. The solvent was removed in vacuum and the residue purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to afford the title compound as a dark pink liquid (0.65 g, 53.4%). 1H NMR (500 MHz, CDCl3): δ 4.02 (s, 2H), 6.24 (t, J=74 Hz, 1H), 6.72 (d, J=8.7, 1H), 6.89 (dd, J=2.7 Hz, 8.8 Hz, 1H), 7.11 (d, J=2.6 Hz, 1H).

Workup

  1. temperatureThe reaction was refluxed for 3 hours
  2. customThe solvent was removed in vacuum
  3. customthe residue purified by silica gel column chromatography
  4. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9937bb53998a45c887bf87d1079debe7
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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