Boron trifluoride → 4-Chloro-2-[(2-chlorophenyl)methyl]aniline

HRID 747610Notes

Reaction equation

HRID 747610 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])=O.C([SiH](CC)CC)C.FB(F)F.[OH-].[Na+]>ClCCl>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([CH2:9][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[CH:4]=1

Participants

6

Reactant 4

HCID 6356Boron trifluorideHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 180692-Amino-2',5-dichlorobenzophenone

Product 1

HCID 143578744-Chloro-2-[(2-chlorophenyl)methyl]anilineYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 10 g of (2-amino-5-chlorophenyl) (2-chlorophenyl)methanone dissolved in 100 ml of dichloromethane are added at room temperature 18.7 ml of triethylsilane and 14.4 ml of trifluoroborane etherate, and the mixture is refluxed for 18 hours and then maintained at room temperature for 72 hours. The resulting mixture is hydrolysed with 2M sodium hydroxide solution, and the phases are separated by settling. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with a cyclohexane/ethyl acetate solvent mixture to give 4.46 g of the expected product.

Workup

  1. temperaturethe mixture is refluxed for 18 hours
  2. customthe phases are separated
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on a column of silica gel
  6. washeluting with a cyclohexane/ethyl acetate solvent mixture

Sources & evidence

ORD record
ord-720fdc28a21a43ea8fd3aa1590dd3528
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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