1,2-Dibromoethane → Methyl 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate

HRID 391325Notes

Reaction equation

HRID 391325 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:16][CH2:17]Br.CCOC(C)=O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:9]([O:11][CH3:12])=[O:10])[CH2:17][CH2:16]2)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 8857Ethyl AcetateHCID 24758Sodium hydride2×HCID 23398394Methyl 2-(5-bromopyridin-3-yl)acetate

Product 1

HCID 59578399Methyl 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2-(5-bromopyridin-3-yl)acetate (4.8 g, 20.86 mmol) in DMF (100 mL) was added 60% NaH in mineral oil (1.1 g, 45.9 mmol), and the mixture was stirred at 0° C. for 15 min. A solution of 1,2-dibromoethane (3.92 g, 20.86 mmol) in DMF (20 mL) was added and the mixture was stirred at room temperature for 1 h. Two other portions of 60% NaH in mineral oil (200 and 450 mg) were added sequentially, until conversion was complete. The mixture was poured into EtOAc (1 L) and washed with water (60 mL), dried over Na2SO4 and concentrated in vacuo to give an oil which was used in next step without further purification.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 h
  2. washwashed with water (60 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give an oil which
  6. customwas used in next step without further purification

Sources & evidence

ORD record
ord-0f03c129449f412eb14b5e30e3558d6f
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

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