1,1-Dibromoethane → HCID 18789971, compound
Reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[OH:14])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:21][CH:22](Br)[CH3:23]>CN(C)C=O>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[O:14][CH2:23][CH2:22][Br:21])(=[O:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A portion (9.6 g, 0.049 mol) of the 2-acetamido-4-nitrophenol produced in (1) above and potassium carbonate (33.86 g, 0.245 mol) were dissolved in dimethylformamide (100 ml), followed by heating at 70° C., addition of dibromoethane (21 ml, 0.245 mol) and stirring for 20 min. Thereafter, the reaction solution was filtered to remove the insoluble matter and the solvent was evaporated, with the residue being thereafter diluted with sodium bicarbonate and subjected to two extractions with ethyl acetate. The organic extracts were dried with sodium sulfate and the solvent was evaporated, with the resulting residue being purified by being subjected to column chromatography on silica gel using, as an eluent, ethyl acetate containing n-hexane (50%) to yield the end compound 1-(2-acetamido-4-nitrophenoxy)-2-bromoethane (8.2 g) as a pale yellow solid mass.
Workup
- filtrationThereafter, the reaction solution was filtered
- customto remove the insoluble matter
- customthe solvent was evaporated, with the residue
- additionbeing thereafter diluted with sodium bicarbonate
- extractionsubjected to two extractions with ethyl acetate
- dry with materialThe organic extracts were dried with sodium sulfate
- customthe solvent was evaporated, with the resulting residue
- custombeing purified
- additionethyl acetate containing n-hexane (50%)
Sources & evidence
- ORD record
- ord-6be2954555c444a1b2832af1e698802d
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06057358
Reaction notes
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