1,2-Dibromoethane → HCID 17620916, compound
Reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Br:17][CH2:18][CH2:19]Br.[NH4+].[Cl-]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:19][CH2:18][Br:17])=[C:6]([CH:9]=1)[CH:7]=[O:8]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 5-bromosalicylaldehyde (5.00 g, 24.87 mmol) in DMF (200 ml) were added K2CO3 (4.47 mg, 32.34 mmol) and 1,2-dibromoethane (46.73 mg, 21.44 ml, 248.73 mmol), followed by stirring at 50° C. for 9 hours. After complete reaction, the solution was cooled to room temperature, cleansed with an aqueous saturated NH4Cl solution and extracted with ethyl acetate. The organic layer thus obtained was additionally washed once with an aqueous saturated NH4Cl solution. Then, the organic layer was dried over anhydrous MgSO4 and filtered, and the filtrate was concentrated in a vacuum. The residue was subjected to column chromatography (ethyl acetate/n-hexane 1/9→1/5) to afford the object compound (yellowish solid, 300 mg, 90.1%).
Workup
- customAfter complete reaction
- temperaturethe solution was cooled to room temperature
- extractionextracted with ethyl acetate
- customThe organic layer thus obtained
- washwas additionally washed once with an aqueous saturated NH4Cl solution
- dry with materialThen, the organic layer was dried over anhydrous MgSO4
- filtrationfiltered
- concentrationthe filtrate was concentrated in a vacuum
- customto afford the object compound (yellowish solid, 300 mg, 90.1%)
Sources & evidence
- ORD record
- ord-2b07e4368ef94e8c8d26d55e7c63499d
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148541B2
Reaction notes
Loading…