Water → tert-Butyl (2-iodo-4-nitrophenoxy)acetate

HRID 542061Notes

Reaction equation

HRID 542061 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].Br[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[I:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 2849492-iodo-4-nitrophenol

Product 1

HCID 57961905tert-Butyl (2-iodo-4-nitrophenoxy)acetateYield 63.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-iodo-4-nitrophenol (2.2 g, 8.3 mmol), tert-butyl bromoacetate (1.6 mL, 11 mmol), and potassium carbonate (2.3 g, 17 mmol) in N,N-dimethylformamide (20 mL) was stirred at 20° C. for 60 h. The reaction mixture was poured into water (300 mL) and extracted with ethyl acetate (500 mL). The organic layer was separated and washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to a crude oil. This material was purified by flash column chromatography to give the desired product (2.0 g, 60%).

Workup

  1. extractionextracted with ethyl acetate (500 mL)
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a crude oil
  7. customThis material was purified by flash column chromatography

Sources & evidence

ORD record
ord-5614f37296884a7eb421e9e45cf08818
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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