Benzyl Bromide → 4-Benzylphenylacetonitrile

HRID 276149Notes

Reaction equation

HRID 276149 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C-:9]#[N:10].[Na+]>>[CH2:2]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:9]#[N:10])=[CH:4][CH:5]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:2]([C:5]1[CH:4]=[C:3]([CH2:2][C:9]#[N:10])[CH:8]=[CH:7][CH:6]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 8929Sodium Cyanide

Product 2

HCID 5975314-BenzylphenylacetonitrileYield 33%HCID 183170103-Benzyl-1-cyanomethylbenzeneYield 9.2%

Procedure

The crude bromomethylbenzene intermediate (19.6 g, 75 mmole) was treated with NaCN as in Example 2 and, after chromatography over silica gel (10 to 100% EtOAc in hexane), 5.2 g (33%) of 4-benzyl-l-cyanomethylbenzene and 1.43 g (9.2%) of 3-benzyl-1-cyanomethylbenzene were obtained, both as oils.

Sources & evidence

ORD record
ord-b9cca87a9ae643d0aae58d57f05daa44
Source dataset
uspto-grants-2002_03
Patent number
US06353128B1

Reaction notes

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