1,2-Dibromoethane → HCID 18693700, compound

HRID 1870835Notes

Reaction equation

HRID 1870835 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+].Br[CH2:22][CH2:23]Br.Cl.O1CCOCC1.[Cl-].[NH4+]>O1CCCC1.CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([C:8]2([C:9]([O:11][CH3:12])=[O:10])[CH2:23][CH2:22]2)[CH:5]=[CH:4][C:3]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

8

Reactant 5

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 14013608HCID 14013608, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 18693700HCID 18693700, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, methyl (2-fluoro-biphenyl-4-yl)-acetate (5.0 g) was dissolved in tetrahydrofuran (50 ml) and then sodium hydride (8.29 g, 60% oily) was added under ice-cooling, after which the resulting mixture was stirred for 30 minutes. Subsequently, N,N-dimethylformamide (100 ml) was added and then 1,2-dibromoethane (17.6 ml) was added, after which the resulting mixture was stirred for 1.5 hours. To the reaction mixture was added 4 N hydrochloric acid-1,4-dioxane solution (60 ml) and the solution was then neutralized with a saturated aqueous ammonium chloride solution and thereafter subjected to extraction with ethyl acetate. The organic layer was dried over sodium sulfate and then concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (hexane/ethyl acetate=20/1), to obtain methyl 1-(2-fluoro-biphenyl-4-yl)-cyclopropanecarboxylate (4.28 g).

Workup

  1. temperaturecooling
  2. stirringafter which the resulting mixture was stirred for 1.5 hours
  3. extractionsubjected to extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a silica gel column chromatography (hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-7417541006cc4f23bb0ab40275686a94
Source dataset
uspto-grants-2000_08
Patent number
US06100260

Reaction notes

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