Triphenylphosphine → Methyl 3-chloro-4-(1,3-difluoropropan-2-yloxy)benzoate

HRID 1964171Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1964171
[F:1][CH2:2][CH:3]([OH:6])[CH2:4][F:5].[Cl:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1O)[C:11]([O:13][CH3:14])=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.CCOC(C)=O>[Cl:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[O:6][CH:3]([CH2:4][F:5])[CH2:2][F:1])[C:11]([O:13][CH3:14])=[O:12]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 679851,3-Difluoro-2-propanolHCID 77580Methyl 3-chloro-4-hydroxybenzoateHCID 5363146Diisopropyl azodicarboxylate

Produkt 1

HCID 67248585Methyl 3-chloro-4-(1,3-difluoropropan-2-yloxy)benzoateAusbeute 131,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1,3-difluoropropan-2-ol (2.57 g, 26.8 mmol) in THF (35 mL) was added methyl 3-chloro-4-hydroxybenzoate (2.00 g, 10.72 mmol), followed by triphenylphosphine (7.03 g, 26.8 mmol) and DIAD (5.21 mL, 26.8 mmol). The reaction was stirred overnight at room temperature, diluted with EtOAc and washed with brine. The organics were separated, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography to give the title compound (3.743 g) as a clear oil. LCMS m/z=265.1 [M+H]+.

Aufarbeitung

  1. washwashed with brine
  2. customThe organics were separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-877f498dcc834f568a4ab3c7a1eb801a
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415484B2

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