1,5-Dibromopentane → 1-(3,4-Dimethoxyphenyl)cyclohexanecarbonitrile

HRID 925115Notes

Reaction equation

HRID 925115 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][C:14]#[N:15])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br>C1COCC1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13]2([C:14]#[N:15])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 667273,4-Dimethoxybenzeneacetonitrile

Product 1

HCID 46393531-(3,4-Dimethoxyphenyl)cyclohexanecarbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

A suspension of sodium hydride (0.3 g, 7.5 mmol, 60% dispersion in oil) in THF (9 mL) was cooled to 0° C. and treated slowly with 2-(3,4-dimethoxyphenyl)acetonitrile (0.532 g, 3 mmol) in THF (3 mL). After stirring for 15 min at this temperature 1,5-dibromopentane (0.49 mL, 3.6 mmol) in THF (3 mL) was added, the bath was removed, and the reaction was left stirring at room temperature for 18 h. The reaction was quenched with saturated aqueous ammonium chloride, extracted with EtOAc and washed with brine. The organic layer was dried (MgSO4), filtered and concentrated to provide 1-(3,4-dimethoxyphenyl)cyclohexanecarbonitrile, which was used without further purification in the next step. MS (ESI) m/z 246 (M+H)+.

Workup

  1. additionwas added
  2. customthe bath was removed
  3. waitthe reaction was left
  4. customThe reaction was quenched with saturated aqueous ammonium chloride
  5. extractionextracted with EtOAc
  6. washwashed with brine
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e98fa809e35f4091a92c6ead18ec4404
Source dataset
uspto-grants-2016_03
Patent number
US09284272B2

Reaction notes

Loading…