1-Bromo-4-fluorobenzene → {3-Cyano-6-[(4-fluorophenyl)carbonyl]phenyl}methyl 2,2-dimethylpropanoate

HRID 413484

Reaktionsgleichung

Reaktionsgleichung von HRID 413484
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.FC1C=CC(Br)=CC=1.[Mg].[C:19]([C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[C:26](=[O:27])[O:25][CH2:24]2)#[N:20].[C:31](Cl)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O.CCCCCCC.C(OCC)C>[C:19]([C:21]1[CH:30]=[CH:29][C:28]([C:26]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:27])=[C:23]([CH:22]=1)[CH2:24][O:25][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])#[N:20]

Komponenten

10

Edukt 6

HCID 99931-Bromo-4-fluorobenzeneHCID 25517Ammonium ChlorideHCID 62493Pivaloyl chlorideHCID 8212181,3-Dihydro-1-oxoisobenzofuran-5-carbonitrileHCID 5462224MagnesiumHCID 178418676HCID 178418676, Verbindung

Produkt 1

HCID 11302208{3-Cyano-6-[(4-fluorophenyl)carbonyl]phenyl}methyl 2,2-dimethylpropanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 21899848Ethylacetate heptaneLösungsmittel

Versuchsvorschrift

A solution of 4-fluorophenylmagnesium bromide, prepared from 4-fluorobromobenzene (19.2 g, 0.11 mol) and magnesium turnings (3.2 g, 0.13 mol) in dry THF (100 mL), was added dropwise to a suspension of 5-cyanophthalid (15.9 g, 0.1 mol) in dry THF (150 mL). The temperature was kept below 5° C. After the addition was complete, the reaction mixture was stirred overnight at room temperature. Pivaloylchloride (13.3 g, 0.11 mol) was added to the reaction mixture and the temperature was raised to 60° C. for 2 hours. The resulting solution was added to a saturated solution of NH4Cl (100 mL, aq) and ice (50 g). Diethylether (100 mL) was added and the phases were separated. The organic phase was washed with 0.1 N NaOH (2×100 mL) and water (100 mL) and the organic phase was dried with MgSO4 (20 g). Evaporation of the solvents gave a crude title compound (29.8 g, 88%) as an oil which was deemed sufficiently pure for further reaction. A pure sample is obtained by crystallisation from EtOAc/n-Heptane (1:9). The title compound is obtained as off white crystals.

Aufarbeitung

  1. customwas kept below 5° C
  2. additionAfter the addition
  3. temperaturethe temperature was raised to 60° C. for 2 hours
  4. customthe phases were separated
  5. washThe organic phase was washed with 0.1 N NaOH (2×100 mL) and water (100 mL)
  6. dry with materialthe organic phase was dried with MgSO4 (20 g)
  7. customEvaporation of the solvents
  8. customgave a crude title compound (29.8 g, 88%) as an oil which
  9. customwas deemed sufficiently pure for further reaction

Quellen und Nachweise

ORD-Eintrag
ord-31b13e3aa43348d48dce776b96465c28
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566540B2

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