Water → Tert-butyl 4-(2-(dimethylamino)ethoxy)-2-nitrobenzoate
Reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].CC(C)([O-])C.[K+].[C:13]([O:17][C:18](=[O:29])[C:19]1[CH:24]=[CH:23][C:22](F)=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27])([CH3:16])([CH3:15])[CH3:14].O>O1CCCC1>[C:13]([O:17][C:18](=[O:29])[C:19]1[CH:24]=[CH:23][C:22]([O:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27])([CH3:16])([CH3:14])[CH3:15]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-dimethylaminoethanol (6.67 mL, 64.8 mmol) in anhydrous tetrahydrofuran (100 mL), at 0° C., potassium tert-butoxide (6.66 g, 59.4 mmol) was added. The mixture was stirred at 0° C. for 1 h, then 4-fluoro-2-nitro-benzoic acid tert-butyl ester (10 g, 41.5 mmol) in anhydrous tetrahydrofuran (50 mL) was added dropwise. After 2 hours at 0° C., the mixture was poured into water (1 L) and extracted with ethyl acetate (4×200 mL). The organic phase was washed with water, brine, dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The crude was purified by flash chromatography, using dichloromethane-methanol-33% NH4OH 9:1:0.01 as eluant, to give the title compound (4.53 g) as yellow oil.
Workup
- waitAfter 2 hours at 0° C.
- extractionextracted with ethyl acetate (4×200 mL)
- washThe organic phase was washed with water, brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated to dryness
- customThe crude was purified by flash chromatography
Sources & evidence
- ORD record
- ord-455c9ee66b704a6684c26eee35ae98b2
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08114865B2
Reaction notes
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