Pyridine → 3-Bromo-5-chlorobenzamide

HRID 471815Notes

Reaction equation

HRID 471815 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5](O)=[O:6].[N:12]1C=CC=CC=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>CC#N>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5]([NH2:12])=[O:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 331283-Bromo-5-chlorobenzoic acidHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 534174713-Bromo-5-chlorobenzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-bromo-5-chlorobenzoic acid (2.88 g; 12.2 mmol; Note 1) and pyridine (1.04 mL; 12.8 mmol) in MeCN (100 mL) at room temperature was added (Boc)2O (3.47 g; 15.9 mmol) in one portion. The mixture was aged 30 min, (NH4)2CO3 was added in one portion. After stirring approximately 16 h at room temperature, volatiles were removed in vacuo. The residue was partitioned between EtOAc/water and the layers were separated. The aqueous layer was extracted with EtOAc (×2), combined organics were washed (10% HCl, brine), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless solid. LC/MS (method A) tR 1.65 min; m/z 234, 236 (M+H, Br isotopes).

Workup

  1. customvolatiles were removed in vacuo
  2. customThe residue was partitioned between EtOAc/water
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc (×2)
  5. washcombined organics were washed (10% HCl, brine)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-2f000385954f489ab2e697f312658a00
Source dataset
uspto-grants-2014_01
Patent number
US08633175B2

Reaction notes

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