1-Bromo-2-Chloroethane → 1-(3-Bromophenyl)cyclopropane-1-carbonitrile

HRID 31497

Reaction equation

HRID 31497 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][C:6]#[N:7].Br[CH2:12][CH2:13]Cl.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2([C:6]#[N:7])[CH2:13][CH2:12]2)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 36023(3-Bromophenyl)acetonitrile

Product 1

HCID 200261781-(3-Bromophenyl)cyclopropane-1-carbonitrile

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

25 g (0.13 mol) of 3-bromo-benzylcyanide are taken up in 32 ml (0.38 mol) of 1-bromo-2-chloro-ethane and combined with 0.6 g (2.6 mmol) of benzyltriethylammonium chloride. Then a solution of 105.8 g (2.65 mol) of sodium hydroxide in 106 ml of water is added dropwise at 10 to 25° C. After 20 hours at 55° C. the reaction solution is poured onto ice water and extracted with ethyl acetate. The organic extracts are dried and evaporated down. The residue is triturated with petroleum ether, suction filtered and dried.

Workup

  1. additionAfter 20 hours at 55° C. the reaction solution is poured onto ice water
  2. extractionextracted with ethyl acetate
  3. customThe organic extracts are dried
  4. customevaporated down
  5. customThe residue is triturated with petroleum ether, suction
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-b3bcfc84b2f1474e97d064fd72e6f4ff
Source dataset
uspto-grants-2008_09
Patent number
US07425641B2

Linked notes

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