Ethyl bromoacetate → Ethyl 2-(4-bromo-2-nitrophenoxy)acetate
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10])[CH3:24]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 4-bromo-2-nitro-phenol (3.28 g, 15.0 mmol, 1 equiv) in dimethylformamide (40 mL) at 23° C. was added potassium carbonate (4.14 g, 30 mmol, 2 equiv) followed by ethyl bromoacetate (1.84 mL, 16.6 mmol, 1.1 equiv). The resulting mixture was warmed to 60° C. (oil bath) for 90 min then cooled to 23° C. The reaction mixture was partitioned between ethyl acetate:heptane (1:1) and water (100 mL each). The organic layer was separated and washed successively with water, saturated brine solution (100 ml, each) then dried (MgSO4), filtered and concentrated to give 4.50 g (11.5 mmol, 77%) of the product as a yellow oil.
Workup
- temperaturethen cooled to 23° C
- customThe reaction mixture was partitioned between ethyl acetate:heptane (1:1) and water (100 mL each)
- customThe organic layer was separated
- washwashed successively with water, saturated brine solution (100 ml
- dry with materialeach) then dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-92a8b32be51c464ba385f2f4b6fddb48
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09023843B2
Reaction notes
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