Water → HCID 18548213, compound

HRID 1265986Notes

Reaction equation

HRID 1265986 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][C:11]2(Br)[CH2:13][C:12]2(Br)Br)=[CH:4][CH:3]=1.C[Li].O>C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH2:9][CH2:10][C:11]2[CH2:13][CH:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 18548192HCID 18548192, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 18548213HCID 18548213, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 0.500 g (0.0011 mol) of 2-(2-(4-chlorophenylthio)ethyl)-1,1,2-tribromocyclopropane in 6 ml of diethyl ether was placed under a nitrogen atmosphere by use of a Firestone valve. While cooling in an ice water bath, 2.38 ml (0.00334 mol) of 1.4 M methyl lithium in diethyl ether was added slowly via 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 0.100 g of 1-(2-(4-chlorophenylthio)ethyl)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-849418a5d8064ec6baccb83362e7cde5
Source dataset
uspto-grants-2003_04
Patent number
US06548448B2

Reaction notes

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