Hydrochloric Acid → Methyl 4-acetoxy-3-bromobenzoate

HRID 572714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572714
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].N1C=CC=CC=1.[C:19](Cl)(=[O:21])[CH3:20].Cl>C(Cl)Cl.O>[C:19]([O:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[Br:1])(=[O:21])[CH3:20]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 4778958Methyl 3-bromo-4-hydroxybenzoate

Produkt 1

HCID 45037033Methyl 4-acetoxy-3-bromobenzoateAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred suspension of methyl 3-bromo-4-hydroxybenzoate (270 g, 1168 mmol) in DCM (1.5 L) was added pyridine (150 mL). Acetyl chloride (87 mL, 1227 mmol) was then added dropwise at room temperature and under nitrogen. The mixture was left to stir for 2 hrs at room temperature. Water (1 L) was then added followed by HCl 2N until pH 1. The organic layer was then washed with water, brine, dried over magnesium sulfate, filtered and evaporated to dryness to afford methyl 4-acetoxy-3-bromobenzoate (300 g, 94%) as a white powder. NMR Spectrum: (DMSOd6) 2.34 (s, 3H), 3.87 (s, 3H), 7.47 (d, 1H), 8.01 (dd, 1H), 8.20 (d, 1H).

Aufarbeitung

  1. waitThe mixture was left
  2. washThe organic layer was then washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-1d970a982c79410db527caef19bb9f82
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029374B2

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