Hydrochloric Acid → HCID 53862169, compound

HRID 1776475Notes

Reaction equation

HRID 1776475 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:18][CH:19]1[CH2:21][CH2:20]1.Cl>CC#N.CCOC(C)=O>[CH:19]1([CH2:18][O:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 81503Bromomethylcyclopropane

Product 1

HCID 53862169HCID 53862169, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-nitrophenol (1 g, 7.19 mmol), K2CO3 (1.192 g, 8.63 mmol), and (bromomethyl)cyclopropane (0.837 ml, 8.63 mmol) in CH3CN (40 ml) was heated to 85° C. overnight. The mixture was portioned between EtOAc and HCl 1N. The organic phase was dried over Na2SO4 and the solvent was removed. 1-(cyclopropylmethoxy)-2-nitrobenzene was obtained as a crude (1.352 g, 7.00 mmol, 97% yield) and used in the next step without further purification.

Workup

  1. dry with materialThe organic phase was dried over Na2SO4
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-f5eb709722784993b97f929057f8ce12
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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