Bromoform → 1,8,8-Tribromo-bicyclo[5.1.0]octane

To a solution of 12 g (6.86 mmol) of 1-bromo-cycloheptene in 52 g (206 mmol) of bromoform and 56 g of methylene chloride was added 0.73 g (1.59 mmol) of N,N′-dibenzyl-N,N,N′,N′-tetramethylethylenediammonium dibromide and 18.8 g (152 mmol) of 45% aqueous potassium hydroxide. After 24 hours 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 0.73 g (1.59 mmol) of N,N′-dibenzyl-N,N,N′,N′-tetramethylethylenediammonium dibromide and 18.8 g (152 mmol) 45% aqueous potassium hydroxide. After 24 hours the reaction mixture was poured onto water. The resulting mixture was transferred to a separatory funnel and the phases were separated. The isolated organic layer was dried over magnesium sulfate and filtered. The filtrate was dried in vacuo. The residue obtained was purified by column chromatography with hexanes. The resulting oil was purified by vacuum distillation to yield 7.8 g of 1,8,8-tribromo-bicyclo[5.1.0]octane.

1. additionAfter 24 hours the reaction mixture was poured onto water
2. customThe resulting mixture was transferred to a separatory funnel
3. customthe phases were separated
4. additionAfter 24 hours the reaction mixture was poured onto water
5. customThe resulting mixture was transferred to a separatory funnel
6. customthe phases were separated
7. dry with materialThe isolated organic layer was dried over magnesium sulfate
8. filtrationfiltered
9. customThe filtrate was dried in vacuo
10. customThe residue obtained
11. customwas purified by column chromatography with hexanes
12. distillationThe resulting oil was purified by vacuum distillation

ORD record

ord-36c4380630644d2289647f5967b1dd56

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07041625B2