Sodium Cyanide → 2-Bromobenzyl cyanide

HRID 1736612Notes

Reaction equation

HRID 1736612 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[C-:10]#[N:11].[Na+]>CS(C)=O.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][C:10]#[N:11]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 769652-Bromobenzyl bromide

Product 1

HCID 296252-Bromobenzyl cyanideYield 81%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

N-Boc-protected 3-[2-(aminoethyl)phenyl]-2-propenoic acid (Compound 23) was prepared as outlined in Scheme IV. A mixture of o-bromobenzyl bromide (10.45 g; 41.81 mmol) and sodium cyanide (2.55 g; 52.25 mmol) in 100 ml of DMSO was heated at 60° C. for 5 hours. After being cooled, the reaction mixture was diluted with 200 ml of water and 200 ml of ethyl acetate. The layers were separated and the aqeous layer was extracted with any additional 100 ml of ethyl acetate. The combined organic layers were dried and concentrated, and the residue was purified on a flash column, eluting with 10% ether/hexane to obtain 6.63 g (81%) of 2-bromobenzyl cyanide 19, 1H NMR (CDCl3): δ3.83 (s, 2H); 7.18 (m,1h); 7.29 (t, 1H); 7.52 (d, 1H); 7.60 (d, 1H).

Workup

  1. temperatureAfter being cooled
  2. customThe layers were separated
  3. extractionthe aqeous layer was extracted with any additional 100 ml of ethyl acetate
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customthe residue was purified on a flash column
  7. washeluting with 10% ether/hexane

Sources & evidence

ORD record
ord-1b1aeb30d1ee4e0a83c83f6befebe1ae
Source dataset
uspto-grants-1996_07
Patent number
US05541286

Reaction notes

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