1,2-Dibromoethane → HCID 59627678, compound

HRID 1930181Notes

Reaction equation

HRID 1930181 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:7]=[C:8]([F:12])[C:9]=1[O:10][CH3:11].Br[CH2:19][CH2:20]Br>CN(C=O)C>[F:3][C:4]1[CH:5]=[C:6]([C:13]2([C:14]([O:16][CH3:17])=[O:15])[CH2:20][CH2:19]2)[CH:7]=[C:8]([F:12])[C:9]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydride2×HCID 67286046HCID 67286046, compound

Product 1

HCID 59627678HCID 59627678, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.326 g, 8.14 mmol) was added in one portion to methyl 2-(3,5-difluoro-4-methoxyphenyl)acetate (1.76 g, 8.14 mmol) in DMF (46.3 mL) at 0° C. under nitrogen. The resulting suspension was stirred at 0° C. for 10 minutes. Following this 1,2-dibromoethane (0.772 mL, 8.96 mmol) was added to the reaction mixture and the solution was stirred for 5 minutes. Additional sodium hydride (0.326 g, 8.14 mmol) was then added and the reaction allowed to stir for 2 hours. The reaction mixture was quenched with saturated NH4Cl (50 mL). The reaction mixture was diluted with EtOAc (75 mL), and washed sequentially with water (4×50 mL) and saturated brine (50 mL). The organic layer was evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution at 10% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford methyl 1-(3,5-difluoro-4-methoxyphenyl)cyclopropanecarboxylate (1.540 g, 78%) as a colourless gum.

Workup

  1. additionwas added to the reaction mixture
  2. stirringthe solution was stirred for 5 minutes
  3. stirringto stir for 2 hours
  4. customThe reaction mixture was quenched with saturated NH4Cl (50 mL)
  5. additionThe reaction mixture was diluted with EtOAc (75 mL)
  6. washwashed sequentially with water (4×50 mL) and saturated brine (50 mL)
  7. customThe organic layer was evaporated
  8. customto afford crude product
  9. customThe crude product was purified by flash silica chromatography, elution at 10% EtOAc in isohexane
  10. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-c3fe4d3bfe434ff8a9e135594af1c2c4
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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