4-Bromo-2-methylaniline → HCID 18404979, compound

HRID 1017783Notes

Reaction equation

HRID 1017783 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[C:14]([CH3:19])[CH:13]=1.[F-].[K+]>C(Cl)Cl>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:16][C:15]1[CH:17]=[CH:18][C:12]([Br:11])=[CH:13][C:14]=1[CH3:19])([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 114234-Bromo-2-methylanilineHCID 738951-Fluoro-2-nitrobenzeneHCID 522689Potassium Fluoride

Product 1

HCID 18404979HCID 18404979, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2.9 ml (27.5 mmol) of 2-fluoro-nitrobenzene, 10.55 g (55 mmol) of 4-bromo-2-methyl-aniline and 1.60 g (27.5 mmol) of spray-dried potassium fluoride is heated to 180° C. After cooling the reaction mixture is taken up in methylene chloride, washed with H2O, with 10% hydrochloric acid and again with H2O, dried with Na2SO4, concentrated and purified by flash chromatography (silica gel; petroleum ether/ethyl acetate=75:25).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. washwashed with H2O, with 10% hydrochloric acid and again with H2O
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. custompurified by flash chromatography (silica gel; petroleum ether/ethyl acetate=75:25)

Sources & evidence

ORD record
ord-8b04c14710014fff8990cbb140825ae0
Source dataset
uspto-grants-2002_11
Patent number
US06479524B1

Reaction notes

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