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

HRID 1453049Notes

Reaction equation

HRID 1453049 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%. 1H NMR (CDCl3) δ: 1.15 (dd, J1=5.31 Hz, J2=2.27 Hz, 2H), 1.48 (dd, J1=5.05 Hz, J2=2.53 Hz, 2H), 6.97-7.12 (m, 3H).

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-9d9e19f34df84da9863e79aa6932cdad
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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