Methanol → Methyl 4-Bromo-2-chlorobenzoate

HRID 60555

Reaktionsgleichung

Reaktionsgleichung von HRID 60555
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:11])[CH:3]=1.S(Cl)(Cl)=O.[CH3:16]O>>[CH3:16][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[Cl:11]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 1088294-Bromo-2-chlorobenzoic acid

Produkt 1

HCID 22058730Methyl 4-Bromo-2-chlorobenzoate

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 4-bromo-2-chlorobenzoic acid (5 g, 21.2 mmol) in 50 mL of methanol was added thionyl chloride (1.4 mL, 19.8 mmol) drop-wise. The reaction was heated to 60° C. After 3 hours the reaction was allowed to cool back to room temperature and concentrated down to give 4-bromo-2-chlorobenzoic acid methyl ester as an orange liquid. Amount obtained: 4.65 g (95%). LCMS (M/Z): 249 (M+H). 1H NMR (Chloroform-d) δ: 3.92 (s, 3 H) 7.45 (dd, J=8.4, 2.0 Hz, 1 H) 7.63 (d, J=2.0 Hz, 1 H) 7.72 (d, J=8.4 Hz, 1 H).

Aufarbeitung

  1. temperatureto cool back to room temperature
  2. concentrationconcentrated down

Quellen und Nachweise

ORD-Eintrag
ord-b419528a08bb49789341d4dafc38a9c9
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440994B2

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