Chloroform → HCID 58155388, compound

HRID 1503183Notes

Reaction equation

HRID 1503183 reaction equation
Br[CH2:2][C:3]1([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[CH2:5][CH2:4]1.[C-:14]#[N:15].[Na+].C(Cl)(Cl)Cl>CS(C)=O.[Cl-].[Na+].O>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([C:3]2([CH2:2][C:14]#[N:15])[CH2:5][CH2:4]2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 8929Sodium CyanideHCID 58155379HCID 58155379, compound

Product 1

HCID 58155388HCID 58155388, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A crude solution of 1-(1-bromomethyl-cyclopropyl)-4-methoxybenzene (60.3 mmol) in dimethyl sulfoxide (60 mL) is treated with sodium cyanide (180.7 mmol). The reaction mixture is heated to 95 degrees Celsius overnight under nitrogen. The reaction mixture is transferred to a separatory funnel using brine (150 mL) and chloroform (300 mL). The reaction mixture is equilibrated and the aqueous layer is removed. The aqueous layer is extracted an additional two times with chloroform (2×300 mL). The combined organic extract is dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to afford [1-(4-methoxyphenyl)cyclopropyl]acetonitrile. This crude material is used in the next step (hydrolysis of the nitrile to the corresponding amide) without further purification. [Alternatively, the corresponding carboxylic acid can be obtained from this material by acid hydrolysis (e.g., using sulfuric acid).]

Workup

  1. temperatureThe reaction mixture is heated to 95 degrees Celsius overnight under nitrogen
  2. customThe reaction mixture is transferred to a separatory funnel
  3. customthe aqueous layer is removed
  4. extractionThe aqueous layer is extracted an additional two times with chloroform (2×300 mL)
  5. extractionThe combined organic extract
  6. dry with materialis dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d69699a8c81b47a1a532bf5ccb0df1df
Source dataset
uspto-grants-2015_12
Patent number
US09212155B2

Reaction notes

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