Ethyl bromoacetate → HCID 57420494, compound
Reaction equation
[N+:1]([C:4]1[C:5]([OH:14])=[C:6]([O:12][CH3:13])[CH:7]=[C:8]([CH:11]=1)[CH:9]=[O:10])([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C=O)C>[CH:9]([C:8]1[CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]([O:14][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:6]([O:12][CH3:13])[CH:7]=1)=[O:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
To a solution of 5-nitrovanilline (591 mg, 3.0 mmol) in DMF (9.0 mL) was added cesium carbonate (2.00 g, 6.16 mmol), followed by ethyl bromoacetate (3.33 mL, 30 mmol). The red mixture was left under stirring at 110° C. until it became yellow, and then for further 3 minutes. After evaporation of DMF under reduced pressure, 22 mL of water were added and the mixture was extracted with dichloromethane (60 mL). The organic phase was washed with brine (15 mL), dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography over silica gel (eluent: dichloromethane) to give 625 mg of a solid (74% yield). 1H NMR (250 MHz, CDCl3): δ 1.30 (t, J=7.2 Hz, 3H), 4.01 (s, 3H), 4.27 (q, J=7.2 Hz, 2H), 4.91 (s, 2H), 7.65 (s, 1H), 7.90 (s, 1H), 9.95 (s, 1H). 13C NMR (63 MHz, CDCl3): δ 14.6, 57.2, 62.0, 70.0, 113.9, 120.4, 132.0, 145.2, 145.9, 154.2, 168.5, 189.3.
Workup
- waitThe red mixture was left
- customAfter evaporation of DMF under reduced pressure, 22 mL of water
- additionwere added
- extractionthe mixture was extracted with dichloromethane (60 mL)
- washThe organic phase was washed with brine (15 mL)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under vacuum
- customThe residue was purified by column chromatography over silica gel (eluent: dichloromethane)
Sources & evidence
- ORD record
- ord-ff33fbcc70ec4977b422280cff214e92
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09212196B2
Reaction notes
Loading…