Ethyl Bromide → 2-Ethoxy-1-methoxy-4-nitro-benzene

HRID 1162189Notes

Reaction equation

HRID 1162189 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[CH3:20]>CN(C=O)C.CCOC(C)=O>[CH2:19]([O:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH3:20]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 694712-Methoxy-5-nitrophenol

Product 1

HCID 117901432-Ethoxy-1-methoxy-4-nitro-benzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

2-methoxy-5-nitro-phenol (508 mg, 3 mmoles) was dissolved in DMF (20 mL) under nitrogen atmosphere. K2CO3 (900 mg, 6.5 mmoles), KI (490 mg, 2.95 mmol) and ethyl bromide (0.250 mL, 3.3 mmoles) were added, and the suspension was heated to 40° C. for 28 hours. The mixture was diluted with AcOEt (60 mL) and extracted with 1N NaOH (40 mL) and water (40 mL). The organic layer was dried over Na2SO4 and evaporated to dryness. The crude was employed in the next step without purification.

Workup

  1. extractionextracted with 1N NaOH (40 mL) and water (40 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated to dryness
  4. customThe crude was employed in the next step without purification

Sources & evidence

ORD record
ord-5b71ee367d584600828d1754b4ae04ae
Source dataset
uspto-grants-2010_10
Patent number
US07820698B2

Reaction notes

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