2-Chloroaniline → HCID 63462513, compound

HRID 1879447Notes

Reaction equation

HRID 1879447 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Cl:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH2:15].[F-].[K+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[Cl:12])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 72402-ChloroanilineHCID 522689Potassium FluorideHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 63462513HCID 63462513, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 1-bromo-4-fluoro-3-nitrobenzene (3.00 mL, 13.6 mmol), 2-chloroaniline (2.87 mL, 27.3 mmol) and potassium fluoride (0.792 g, 13.6 mmol) was heated at 180° C. for 48 h. Upon cooling the mixture, DCM (300 mL) was added and the mixture was successively washed with water (100 mL), 10% HCl (2×50 mL) and brine (50 mL). The resulting organic solution was dried over magnesium sulfate and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography on SiO2(DCM:hexanes=25:75) to afford the title compound as a red crystalline solid. MS (ESI, pos. ion) m/z: 328.9 (M+1).

Workup

  1. additionwas added
  2. washthe mixture was successively washed with water (100 mL), 10% HCl (2×50 mL) and brine (50 mL)
  3. dry with materialThe resulting organic solution was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude material was purified by flash chromatography on SiO2(DCM:hexanes=25:75)

Sources & evidence

ORD record
ord-2d8f2a6fc4604b8ba959c63075c6950a
Source dataset
uspto-grants-2012_11
Patent number
US08314131B2

Reaction notes

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