Water → HCID 11275195, compound

HRID 1265972Notes

Reaction equation

HRID 1265972 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2(Br)[CH2:11][C:10]2(Br)Br)=[CH:4][CH:3]=1.C[Li].O>C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH2:10][CH:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12074416HCID 12074416, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 11275195HCID 11275195, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1.20 g (0.00298 mol) of 2-(4-chlorophenylmethyl)-1,1,2-tribromocyclopropane in 6 ml of diethyl ether was placed under a nitrogen atmosphere via use of a Firestone valve. While cooling in an ice water bath, 6.38 ml (0.00893 mol) of 1.4M methyl lithium in diethyl ether was added slowly by syringe. After 15 minutes, 2 ml of water was added via syringe. The resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was dried over MgSO4 and filtered. The solvent was removed from the filtrate in vacuo with a bath temperature under 20° C. to yield 0.430 g of 1-(4-chlorophenylmethyl)-cyclopropene as an oil.

Workup

  1. temperatureWhile cooling in an ice water bath
  2. customThe resulting mixture was transferred to a separatory funnel
  3. customthe phases were separated
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed from the filtrate in vacuo with a bath temperature under 20° C.

Sources & evidence

ORD record
ord-6fdab535d3d74b38b0268893c9bfae4e
Source dataset
uspto-grants-2003_04
Patent number
US06548448B2

Reaction notes

Loading…