p-Toluenesulfonic acid → Methyl 3-bromo-2-fluorobenzoate

HRID 413175

Reaktionsgleichung

Reaktionsgleichung von HRID 413175
[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:12]OC(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:12])=[O:6]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 27363133-Bromo-2-fluorobenzoic acid

Produkt 1

HCID 21584505Methyl 3-bromo-2-fluorobenzoateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 3-bromo-2-fluorobenzoic acid (0.219 g, 1 mmol) in dry methanol (5 mL) under nitrogen was treated with trimethylorthoformate (0.22 mL, 2 mmol) and p-toluenesulfonic acid (catalytic amount), and then heated under reflux. After 16 h, the mixture was evaporated and the residue partitioned between water and Et2O. the organic layer was washed with sat. sodium hydrogen carbonate solution, water, brine, dried (MgSO4) and evaporated to give methyl 3-bromo-2-fluorobenzoate (0.195 g, 0.84 mmol, 84%): 1H-NMR (CDCl3) δ7.90-7.85 (m, 1H), 7.71-7.65 (m, 1H), 7.10 (dt, 1H, J=8.0, 1.0 Hz), 3.94 (s, 3H): MS (EI) 232 (M+).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux
  3. customthe mixture was evaporated
  4. customthe residue partitioned between water and Et2O
  5. washthe organic layer was washed with sat. sodium hydrogen carbonate solution, water, brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-41d7a8e3aab14b49a84d863e7faaf206
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566358B2

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