Benzyl Bromide → 3-Benzyloxy-2,2-dimethylpropionitrile

HRID 342596Notes

Reaction equation

HRID 342596 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]([CH3:9])([CH3:8])[C:6]#[N:7].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCCCCC.CN(C=O)C.O>[CH2:10]([O:3][CH2:4][C:5]([CH3:9])([CH3:8])[C:6]#[N:7])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 135313833-Hydroxy-2,2-dimethylpropanenitrile

Product 1

HCID 542383773-Benzyloxy-2,2-dimethylpropionitrileYield 95%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 60% sodium hydride (367.1 mg, 15.3 mmol) was washed with hexane (3×2 mL) and suspended in DMF (2 mL). The suspension was cooled to -10° C. and then a mixture of 3-hydroxy-2,2-dimethylpropanenitrile (1.4 g, 13.9 mmol) and DMF (8 mL) was added. The mixture was cooled 2.5 hour with stirring stirred at -10° to -5° C. and then benzyl bromide (1.7 mL, 13.9 mmol) was added. The mixture was cooled 2 hours with stirring at -5° C., diluted with water (10 mL) and extracted with diethyl ether (3×10 mL). The combined extracts were washed with water (1×10 mL) and brine (1×10 mL), dried (MgSO4) and concentrated to give 3-benzyloxy-2,2-dimethylpropanenitrile (2.5 g, 13.2 mmol).

Workup

  1. additionwas added
  2. temperatureThe mixture was cooled 2.5 hour
  3. stirringstirred at -10° to -5° C.
  4. temperatureThe mixture was cooled 2 hours
  5. stirringwith stirring at -5° C.
  6. extractionextracted with diethyl ether (3×10 mL)
  7. washThe combined extracts were washed with water (1×10 mL) and brine (1×10 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8a94fd59343244beb114c268be6fad62
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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