tert-Butyl bromoacetate → Tert-butyl 2-(3-nitro-4-phenylphenoxy)acetate

HRID 1518638Notes

Reaction equation

HRID 1518638 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:16])[CH:7]=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([O-:3])=[O:2].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[O:16][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 121698073-Nitro-4-phenylphenol

Product 1

HCID 66596949Tert-butyl 2-(3-nitro-4-phenylphenoxy)acetateYield 112.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3-Nitro-4-phenylphenol (215 mg, 1.0 mmol) was dissolved in N,N-dimethylformamide (5 mL) and tert-butyl 2-bromoacetate (292 mg, 1.5 mmol) was added thereto. After stirring at 80° C. for 18 hours, the reaction solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography to obtain tert-butyl 2-(3-nitro-4-phenylphenoxy)acetate (370 mg).

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-ac5a7a074923490089c1008cefb532ee
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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