4-Nitrophenol → 1-(Cyclopropylmethoxy)-4-nitrobenzene

HRID 594817Notes

Reaction equation

HRID 594817 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:12][CH:13]1[CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH:13]1([CH2:12][O:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 81503Bromomethylcyclopropane

Product 1

HCID 111715331-(Cyclopropylmethoxy)-4-nitrobenzeneYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

4-Nitrophenol (5.0 g, 35.9 mmol) was added to a suspension of (bromomethyl)cyclopropane (10.7 g, 79.07 mmol) and K2CO3 (19.9 g, 143.76 mmol) in DMF (80 mL), and the reaction was stirred at 40° C. overnight. The reaction mixture was diluted with water (300 mL) and extracted with EtOAc (100 mL×3). Organics were washed with brine (50 mL), dried (Na2SO4), and concentrated. The residue was purified by silica gel chromatography (0-5% EtOAc/PE) to give 6.77 g (98%) of the title compound as a colorless oil. [M+H] Calc'd for C10H11NO3, 194. Found, 194.

Workup

  1. extractionextracted with EtOAc (100 mL×3)
  2. washOrganics were washed with brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (0-5% EtOAc/PE)

Sources & evidence

ORD record
ord-c9402e36facf48b8906c545a4df31f95
Source dataset
uspto-grants-2016_01
Patent number
US09242968B2

Reaction notes

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