1,2-Dibromoethane → HCID 67997471, compound

HRID 1425991Notes

Reaction equation

HRID 1425991 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][N:9]=1)[CH3:4].Br[CH2:17][CH2:18]Br>CN(C)C=O>[CH2:3]([O:5][C:6]([C:7]1([C:8]2[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][N:9]=2)[CH2:18][CH2:17]1)=[O:15])[CH3:4]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 53419398Ethyl 2-(4-broMopyridin-2-yl)acetate

Product 1

HCID 67997471HCID 67997471, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (55% in mineral oil, 0.72 g) was added to a solution of (4-bromo-pyridin-2-yl)-acetic acid ethyl ester (1.80 g) in N,N-dimethylformamide (20 mL) chilled in an ice bath. The resulting mixture was stirred for 10 min at room temperature and then cooled again in an ice bath. 1,2-Dibromoethane (0.70 mL) was added dropwise and the cooling bath was removed. The mixture was stirred at room temperature overnight. Brine was added and the resulting mixture was extracted with ethyl acetate. The combined extracts were washed with brine and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel (cyclohexane/ethyl acetate 95:5→1:1) to give the title compound as an oil. Yield: 1.28 g (64% of theory); Mass spectrum (ESI+): m/z=270/272 (Br) [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. temperaturecooled again in an ice bath
  3. customthe cooling bath was removed
  4. stirringThe mixture was stirred at room temperature overnight
  5. additionBrine was added
  6. extractionthe resulting mixture was extracted with ethyl acetate
  7. washThe combined extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. customThe solvent was evaporated
  10. customthe residue was chromatographed on silica gel (cyclohexane/ethyl acetate 95:5→1:1)

Sources & evidence

ORD record
ord-b7ee2a6cfb394b129e5ef4320d709a52
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

Loading…