Benzyl Bromide → 2-(3-(Benzyloxy)propyl)benzonitrile

HRID 337156Notes

Reaction equation

HRID 337156 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8].[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C.O>[CH2:15]([O:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 666899522-(3-Hydroxypropyl)benzonitrile

Product 1

HCID 666886992-(3-(Benzyloxy)propyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(3-hydroxypropyl)benzonitrile (Example 323c, 3.83 g) in DMF (40 mL) under nitrogen was treated with 60% Sodium hydride (1.140 g) and stirred at room temperature for 1 h before adding benzyl bromide (2.83 mL). The resulting solution was stirred at 20° C. for 60 h. The reaction mixture was diluted with water (200 mL), and extracted with ethyl acetate (200 mL). The organic was dried (MgSO4), filtered and evaporated. The residue was purified (SiO2 chromatography eluting with 30% diethyl ether in isohexane). Pure fractions were evaporated to dryness to afford the subtitle compound as an oil (2.3 g).

Workup

  1. stirringThe resulting solution was stirred at 20° C. for 60 h
  2. extractionextracted with ethyl acetate (200 mL)
  3. dry with materialThe organic was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified
  7. wash(SiO2 chromatography eluting with 30% diethyl ether in isohexane)
  8. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-9f3d0f08c1194ad59fd5df6303fab2e7
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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