Bromoform → HCID 18548204, compound

HRID 1265977Notes

Reaction equation

HRID 1265977 reaction equation
[CH3:1][C:2]([C:10]([Cl:12])=[CH2:11])([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:13]([Br:16])(Br)[Br:14].[OH-].[K+]>C(Cl)Cl>[CH3:9][C:2]([C:10]1([Cl:12])[CH2:11][C:13]1([Br:16])[Br:14])([CH3:1])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 5558BromoformHCID 14797Potassium HydroxideHCID 18548217HCID 18548217, compound

Product 1

HCID 18548204HCID 18548204, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100 ml round bottomed flask equipped with magnetic stirring was added 4.5 g (25 mmol) of 1-(α,α-dimethylbenzyl)-1-chloroethylene, 25 g (100 mmol) of bromoform, 27 g of methylene chloride, 0.37 g of N,N′-dibenzyl-N,N,N′N′-tetramethylethylenediammonium dibromide, and 12.4 g (100 mmol) of 45% aqueous KOH. Rapid stirring overnight gave a 20% conversion to the desired cyclopropane. Washing the aqueous layer with water and resubmitting with fresh bromoform, catalyst, and KOH overnight gave further conversion. A third submission was deemed adequate. The aqueous washed organic layer was evaporated in vacuo and chromatographed on silica gel using 2% diethyl ether in hexane yielding 4.2 g of 1-(α,α-dimethylbenzyl)-1-chloro-2,2-dibromocyclopropane.

Workup

  1. customInto a 100 ml round bottomed flask equipped
  2. stirringRapid stirring overnight

Sources & evidence

ORD record
ord-4b1dcfaa72b34daab64ccf3d36d6d4b0
Source dataset
uspto-grants-2003_04
Patent number
US06548448B2

Reaction notes

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