Ethyl Acetate → 3,5-Dichloro-4-(4-fluoro-3-methyl-phenoxy)-nitrobenzene

HRID 1265161

Reaktionsgleichung

Reaktionsgleichung von HRID 1265161
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[K+].I[C:13]1[C:18]([Cl:19])=[CH:17][C:16]([N+:20]([O-:22])=[O:21])=[CH:15][C:14]=1[Cl:23].CCOC(C)=O>CN1CCCC1=O>[Cl:19][C:18]1[CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=[C:14]([Cl:23])[C:13]=1[O:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([CH3:1])[CH:3]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 112948Benzene, 1,3-dichloro-2-iodo-5-nitro-HCID 27373944-Fluoro-3-methylphenol

Produkt 1

HCID 186142743,5-Dichloro-4-(4-fluoro-3-methyl-phenoxy)-nitrobenzeneAusbeute 82,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 3-methyl-4-fluorophenol (99 mg, 0.79 mmol), potassium hydroxide (53 mg, 0.94 mmol), 4-iodo-3,5-dichloro-nitrobenzene (250 mg, 0.79 mmol) and 4A° molecular sieves (75 mg) in N-methylpyrolidinone (3 mL) was stirred at 130° C. for 2 h. The reaction mixture was poured into ice cold 1 N HCl (20 mL) and EtOAc (25 mL) was added. The EtOAc phase was separated and washed with 1N HCl (3×25 mL) and brine (25 mL). The EtOAc solution was dried over Na2SO4, filtered and concentrated. The residue was purified by preparative TLC (Hexanes: CH2Cl2=7:3) to afford 3,5-dichloro-4-(4-fluoro-3-methyl-phenoxy)-nitrobenzene (207 mg). MS Calc.: 315.0 Found: 315.0 (M).

Aufarbeitung

  1. additionwas added
  2. customThe EtOAc phase was separated
  3. washwashed with 1N HCl (3×25 mL) and brine (25 mL)
  4. dry with materialThe EtOAc solution was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative TLC (Hexanes: CH2Cl2=7:3)

Quellen und Nachweise

ORD-Eintrag
ord-963df51208f8457fab8547ffcd02c8cb
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06545018B2

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