Acetic Acid → HCID 10640949, compound

HRID 1354841Notes

Reaction equation

HRID 1354841 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Br:9])[CH:8]=1)[NH2:5].[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl>[CH2:10]([NH:5][C:4]1[CH:3]=[C:2]([Br:1])[CH:8]=[C:7]([Br:9])[CH:6]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 2215123,5-DibromoanilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 10640949HCID 10640949, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The same procedure as described above was used in a scale up reaction where 3,5-dibromoaniline (273) (3.85 g, 15.35 mmol), benzaldehyde (274) (1.61 g, 15.35 mmol), Na(OAc)3BH (6.47 g, 30.7 mmol), AcOH (1.11 g, 18.42 mmol) and DCE (38 mL) were used. After 3 h reaction and purification (flash chromatography), benzyl-(3,5-dibromo-phenyl)-amine (275) (3.64 g, 10.67 mmol) was obtained in 69.6% isolated yield.

Workup

  1. customAfter 3 h reaction and purification (flash chromatography)

Sources & evidence

ORD record
ord-f0d4284c989f4e7cbb59cd6ba0f609e3
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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