Dimethylformamide → 5-Bromo-3,3,7-trimethyl-2,3-dihydro-benzofuran

HRID 402772

Reaktionsgleichung

Reaktionsgleichung von HRID 402772
[CH3:1][C:2](=[CH2:14])[CH2:3][O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([Br:12])=[CH:7][C:6]=1Br.CC([O-])=O.[K+].C(O[Na])=O.CN(C=O)C>[N+](CC)(CC)(CC)CC.[Cl-].O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]2[O:4][CH2:3][C:2]([CH3:14])([CH3:1])[C:6]=2[CH:7]=1

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 517044Potassium AcetateHCID 154540742,4-Dibromo-6-methylphenyl 2-methylprop-2-en-1-yl etherHCID 178526064HCID 178526064, Verbindung

Produkt 1

HCID 154540765-Bromo-3,3,7-trimethyl-2,3-dihydro-benzofuranAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 5946Tetraethylammonium ChlorideKatalysatorHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a nitrogen flushed 100 mL round bottom flask were added 2,4-dibromo-6-methylphenyl 2-methylprop-2-en-1-yl ether (710 mg, 2.22 mmol), Pd(dppf)Cl2 (36 mg, 0.044 mmol), Et4NCl (490 mg, 2.66 mmol), KOAc (544 mg, 5.55 mmol), HCO2Na (181 mg, 2.66 mmol), DMF (20 mL) and water (1 mL). The reaction mixture was heated at 75° C. overnight. After cooling to room temperature, it was diluted with water and extracted with EtOAc/hexanes (1:3). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified on a silica gel column eluting with a gradient of 100% hexanes to 10% EtOAc/hexanes to give the title intermediate (110 mg, 70% purity) as light yellow liquid.

Aufarbeitung

  1. customTo a nitrogen flushed 100 mL round bottom flask
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with EtOAc/hexanes (1:3)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on a silica gel column
  8. washeluting with a gradient of 100% hexanes to 10% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-9361579a0c8e451a83a487b13e3e2b32
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742110B2

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