4-Chloro-3-nitroanisole → HCID 53399269, compound

HRID 2421235Notes

Reaction equation

HRID 2421235 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-])=O.[CH:13]([Mg]Br)=[CH2:14]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]2[C:3]=1[NH:10][CH:14]=[CH:13]2

Participants

4

Reactant 2

HCID 251404-Chloro-3-nitroanisoleHCID 178418507HCID 178418507, compound

Product 1

HCID 53399269HCID 53399269, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 4-chloro-3-nitroanisole (6.0 g, 32.0 mmol) in tetrahydrofuran (140 mL) at −40° C. was added vinylmagnesium bromide (1M in tetrahydrofuran, 112 mL, 112.0 mmol). The mixture was stirred at −40° C. for 1.5 hours and then quenched by the addition of saturated aqueous ammonium chloride solution (150 mL). The reaction mixture was allowed to warm to room temperature and then the product extracted into ethyl acetate (×2). The combined organic layers were dried over magnesium sulphate, filtered and concentrated at reduced pressure. The product was purified by silica gel chromatography eluting with 2-15% ethyl acetate in hexane to yield the title compound (D11), (1.67 g).

Workup

  1. customquenched by the addition of saturated aqueous ammonium chloride solution (150 mL)
  2. temperatureto warm to room temperature
  3. extractionthe product extracted into ethyl acetate (×2)
  4. dry with materialThe combined organic layers were dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customThe product was purified by silica gel chromatography
  8. washeluting with 2-15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-eec27f1ccb5d48299ca8a10eae1ca478
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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