3-Fluoro-4-methylaniline → HCID 178426501, compound

HRID 1864482Notes

Reaction equation

HRID 1864482 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[C:8]#[N:9].[F:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[CH3:22])[NH2:18]>C(Cl)(Cl)Cl>[Br:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[C:8](=[NH:9])[NH:18][C:17]1[CH:19]=[CH:20][C:21]([CH3:22])=[C:15]([F:14])[CH:16]=1

Participants

5

Reactant 3

HCID 99573-Fluoro-4-methylanilineHCID 162722-BromobenzonitrileHCID 6451240Aluminum(III) Chloride

Product 1

HCID 178426501HCID 178426501, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

Solid aluminum chloride (3.66 g, 27.5 mmol, 1 equiv) was added to a neat mixture of 2-bromobenzonitrile (1-1, 5.0 g, 27.5 mmol, 1.0 equiv) and 3-fluoro-4-methylaniline (3.44 g, 27.5 mmol, 1.00 equiv) at 80° C., and the resulting mixture was heated at 140° C. for 30 min. The reaction mixture was cooled to 23° C., allowed to stand for 14 h, then dissolved in chloroform (35 mL). The solution was washed with aqueous NaHCO3 solution (40 mL) and concentrated to afford 2-bromo-N-(3-fluoro-4-methylphenyl)benzenecarboximidamide (1-2) as a dark oil. LRMS m/z: Calc'd for C14H12BrFN2 (M+H) 308.2, found 308.2.

Workup

  1. temperatureThe reaction mixture was cooled to 23° C.
  2. washThe solution was washed with aqueous NaHCO3 solution (40 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ecfad19783f649b19437065c00a02aef
Source dataset
uspto-grants-2009_12
Patent number
US07625912B2

Reaction notes

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