Methane → 3-(4-bromophenyl)-3-oxopropanenitrile

HRID 1180586Notes

Reaction equation

HRID 1180586 reaction equation
[C-:1]#[N:2].[K+].Br[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1)=[O:7].C.Cl>O.C(O)C>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:6](=[O:7])[CH2:5][C:1]#[N:2])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 74544-Bromophenacyl bromideHCID 9032Potassium Cyanide

Product 1

HCID 7703123-(4-bromophenyl)-3-oxopropanenitrileYield 47.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution containing 9.4 g of KCN in 20 ml of water is prepared and then it is poured dropwise over a mixture containing 20 g of 2-bromo-1-(4-bromophenyl)ethanone dissolved in 800 ml of 90% ethanol. After stirring for 5 hours at RT, the solid formed is filtered and then it is rinsed with ice-cold water. The solid obtained is dissolved in 400 ml of water and then activated charcoal is added, the mixture is kept stirring for 20 minutes, and then filtered on Celite®. The filtrate obtained is treated with HCl at 10% and the white precipitate formed is filtered, washed with water and then dried under vacuum. 7.63 g of the expected compound are obtained. m.p.=164° C.

Workup

  1. customis prepared
  2. additionit is poured dropwise over a mixture
  3. customthe solid formed
  4. filtrationis filtered
  5. washit is rinsed with ice-cold water
  6. customThe solid obtained
  7. stirringthe mixture is kept stirring for 20 minutes
  8. filtrationfiltered on Celite®
  9. customThe filtrate obtained
  10. customthe white precipitate formed
  11. filtrationis filtered
  12. washwashed with water
  13. customdried under vacuum

Sources & evidence

ORD record
ord-db86e4a40a524442ad047c3665a258d7
Source dataset
uspto-grants-2007_10
Patent number
US07282516B2

Reaction notes

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