Borane;tetrahydrofuran → (4-Chloro-3-fluoro-5-nitrophenyl)methanamine

HRID 1258742Notes

Reaction equation

HRID 1258742 reaction equation
B.C1COCC1.[Cl:7][C:8]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=1[F:19]>C1COCC1>[Cl:7][C:8]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:11]([CH2:12][NH2:13])=[CH:10][C:9]=1[F:19]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 679578694-Chloro-3-fluoro-5-nitrobenzonitrile

Product 1

HCID 67957867(4-Chloro-3-fluoro-5-nitrophenyl)methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of BH3/THF (7.5 mL; 7.5 mmol) was added dropwise to a solution of 4-chloro-3-fluoro-5-nitrobenzonitrile (750 mg; 3.74 mmol) in THF (5 mL) at 0° C. The mixture was stirred at 0° C. for 3 h, it was acidified to pH ˜1 and stirred at rt for 1 h and then basicified to pH ˜8 and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was dissolved in Et2O and precipitated with PE to give the sub-title compound.

Workup

  1. stirringstirred at rt for 1 h
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in Et2O
  7. customprecipitated with PE

Sources & evidence

ORD record
ord-698ba325855e41bfa5c2f49f178222bc
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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