Methyl 3-bromo-5-formylbenzoate → Methyl 3-bromo-5-vinylbenzoate

HRID 1845308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845308
[CH2:1]([Li])CCC.[Br:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([CH:17]=O)[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Br:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([CH:17]=[CH2:1])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]

Komponenten

5

Edukt 2

HCID 11436457Methyl 3-bromo-5-formylbenzoateHCID 178418339Butyllithium

Produkt 1

HCID 58188041Methyl 3-bromo-5-vinylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of methyltriphenylphosphonium bromide (350 mg, 0.97 mmol) in THF (3 mL) at −78° C. under nitrogen was added dropwise 2.5 M of n-butyllithium in tetrahydrofuran (0.31 mL, 0.78 mmol). The mixture was gradually warmed until a yellow color persisted. The mixture was cooled to 0° C. and a solution of methyl 3-bromo-5-formylbenzoate (157 mg, 0.65 mmol) in THF (2 mL) was added dropwise. After being stirred for 20 min at 0° C., the mixture was quenched with saturated aq. NH4Cl and extracted with EtOAc. The organic layer was separated and washed with brine, dried, and concentrated. The residue was purified by flash column to afford the title compound.

Aufarbeitung

  1. temperatureThe mixture was gradually warmed until a yellow color
  2. customthe mixture was quenched with saturated aq. NH4Cl
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by flash column

Quellen und Nachweise

ORD-Eintrag
ord-86c45a0e9602481894e034d3a0e12f67
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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