N-bromobutanimide → HCID 12452842, compound
Reaction equation
[C:1]([C:4](=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:3])[CH3:2].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:2][C:1]1[O:3][C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4.33 g (0.02 mole) ethyl 2-acetyl-2-nonenoate and 3.57 g (0.02 mole) N-bromosuccinimide in 50 ml of carbon tetrachloride was heated at reflux for 12 hours. After cooling, the succinimide was removed by filtration and the solution concentrated in vacuo. Distillation of the crude product gave 3.09 g (69%) of ethyl 2-methyl-5-pentyl-3-furoate, bp 115°-119° C. (1.3 mm).
Workup
- temperaturewas heated
- temperatureat reflux for 12 hours
- temperatureAfter cooling
- customthe succinimide was removed by filtration
- concentrationthe solution concentrated in vacuo
- distillationDistillation of the crude product
Sources & evidence
- ORD record
- ord-2f17ab33e8794a20b8624152d4c6845e
- Source dataset
- uspto-grants-1977_05
- Patent number
- US04025537
Reaction notes
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