1,2-Dibromoethane → 1-(4-Bromo-2-fluorophenyl)cyclopropane-1-carbonitrile

HRID 858601Notes

Reaction equation

HRID 858601 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[C:6]([F:13])[CH:5]=1.Br[CH2:15][CH2:16]Br>CN(C=O)C.C1COCC1.CCOC(C)=O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:11]#[N:12])[CH2:16][CH2:15]2)=[C:6]([F:13])[CH:5]=1

Participants

7

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 71723082-(4-Bromo-2-fluorophenyl)acetonitrile

Product 1

HCID 587623291-(4-Bromo-2-fluorophenyl)cyclopropane-1-carbonitrile

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a slurry of sodium hydride (60% dispersion in mineral oil, 0.82 g, 20.6 mmol) in DMF (20 mL) cooled to 0° C. was added a solution of (4-bromo-2-fluoro-phenyl)-acetonitrile (2.0 g, 9.35 mmol) from Step 1 above dissolved in THF (10 mL). The reaction was stirred till gas evolution ceased, and then 1,2-dibromoethane (1.8 mL, 20.6 mmol) was added slowly. The reaction was stirred for 30 minutes, and then diluted with 100 mL EtOAc. The solids were removed by filtration, and the organic layer was washed with 100 mL water. The organic layer was dried over MgSO4, and then filtered. The mother liquor was concentrated by rotary evaporation, and the product was distilled under high vacuum (0.3 torr, 45° C.). Yield: 0.98 g, 44%.

Workup

  1. stirringThe reaction was stirred for 30 minutes
  2. customThe solids were removed by filtration
  3. washthe organic layer was washed with 100 mL water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationThe mother liquor was concentrated by rotary evaporation
  7. distillationthe product was distilled under high vacuum (0.3 torr, 45° C.)

Sources & evidence

ORD record
ord-12711fcd3fee41e5987003e9d6875ff4
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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