Methanol → 2-(2-hydroxy-4-methoxyphenyl)-N-methylacetamide

HRID 1782031

Reaktionsgleichung

Reaktionsgleichung von HRID 1782031
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][C:12]([NH:14][CH3:15])=[O:13].B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][C:12]([NH:14][CH3:15])=[O:13].[OH:9][C:7]1[CH:6]=[CH:5][C:4]([CH2:11][C:12]([NH:14][CH3:15])=[O:13])=[C:3]([O:2][CH3:1])[CH:8]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 25134Boron tribromideHCID 8180193HCID 8180193, Verbindung

Produkt 2

HCID 690173522-(2-hydroxy-4-methoxyphenyl)-N-methylacetamideHCID 69019532HCID 69019532, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-(2,4-dimethoxyphenyl)-N-methylacetamide (445 mg, 2.12 mmol) in CH2Cl2 (10 mL) was slowly added 1M BBr3 solution in CH2Cl2 (6.4 mL, 6.4 mmol). After addition was completed, the reaction mixture was stirred at 0° C. for 2.5 h, methanol (2 mL) was added and after 15 min the volatiles were removed in vacuo. The residue was dissolved in ethyl acetate, washed successively with aqueous NaHCO3 and H2O. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-5% methanol in dichloromethane) to give the subtitled compound (16 mg) along with 2-(4-hydroxy-2-methoxyphenyl)-N-methylacetamide (30 mg).

Aufarbeitung

  1. additionAfter addition
  2. customwere removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed successively with aqueous NaHCO3 and H2O
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel flash chromatography (0-5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-4df6b0a2d19445ef82ebb5c8053a5c34
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07498338B2

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