1-Bromo-2-Chloroethane → Methyl 3-(1-cyanocyclopropyl)benzoate

HRID 1184843Notes

Reaction equation

HRID 1184843 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])#[N:2].[H-].[Na+].Br[CH2:17][CH2:18]Cl>CS(C)=O>[C:1]([C:3]1([C:4]2[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=2)[C:7]([O:9][CH3:10])=[O:8])[CH2:18][CH2:17]1)#[N:2]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 10821136Methyl 3-(cyanomethyl)benzoate

Product 1

HCID 57441038Methyl 3-(1-cyanocyclopropyl)benzoateYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of methyl 3-(cyanomethyl)benzoate 1 (2 g, 11.4 mmol) in DMSO (30 mL) was added NaH (60%, 913 mg, 23 mmol) in one portion. 1-bromo-2-chloroethane (1.164 mL, 11.4 mmol) was added slowly at 0° C. and stirring continued for 18 h at 25° C. The reaction was quenched with water, extracted with EtOAc, dried, and evaporated. Compound dissolved again in EtOAc and washed with NaHCO3 solution, brine, dried and concentrated to affording methyl 3-(1-cyanocyclopropyl)benzoate 33 (1.56 g, 68%). NMR (400 MHz, CDCl3) 1.47 (m, 2H), 1.78 (m, 2H), 3.93 (s, 3H), 7.45 (t, J=7.8 Hz, 1H), 7.59 (m, 1H), 7.88 (t, J=1.6 Hz, 1H), 7.97 (m, 1H).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. customdried
  4. customevaporated
  5. dissolutionCompound dissolved again in EtOAc
  6. washwashed with NaHCO3 solution, brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-808cbaf940114652a9d20afafaf2a441
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

Loading…