Bromoform → 1,1,2-Tribromo-2-[2-(1-ethoxy-ethoxy)ethyl]-cyclopropane

To a solution of 14.02 g (0.0628 mol) 2-bromo-4-(1-ethoxy-ethoxy)-but-1-ene in 108 ml methylene chloride with 0.5-0.9 ml 45% aqueous potassium hydroxide was added 16.4 ml (0.118 mol) of bromoform and 2.88 g (0.00628 mol) of N,N′-dibenzyl-N,N,N′,N′-tetramethylethylenediammonium dibromide and 28 ml (0.314 mol) 45% aqueous potassium hydroxide. After 3 days the reaction mixture was poured onto water. The resulting mixture was transferred to a separatory funnel and the phases were separated. To the isolated organic layer was added 2.88 g (0.00628 mol) of N,N′-dibenzyl-N,N,N′,N′-tetramethylethylenediammonium dibromide and 28 ml (0.314 mol) 45% aqueous potassium hydroxide. After 24 hours, hexanes and water were added. This mixture was gravity filtered through qualitative fluted filter paper. 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 to yield 17.0 g of 1,1,2-tribromo-2-[2-(1-ethoxy-ethoxy)-ethyl]-cyclopropane as an oil.

1. additionAfter 3 days the reaction mixture was poured onto water
2. customThe resulting mixture was transferred to a separatory funnel
3. customthe phases were separated
4. filtrationfiltered through qualitative fluted filter paper
5. customThe resulting mixture was transferred to a separatory funnel
6. customthe phases were separated
7. dry with materialThe organic layer was dried over MgSO4
8. filtrationfiltered
9. customThe solvent was removed from the filtrate in vacuo

ORD record

ord-a7f1c8811e594589b8193095b6cdcfdf

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06548448B2