Triphenylphosphine → 2-Bromo-4-methyl-1-((3-methylpent-4-en-2-yl)oxy)benzene

HRID 1400757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400757
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH3:10][CH:11]([CH:15]=[CH2:16])[CH:12](O)[CH3:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[O:9][CH:15]([CH:11]([CH3:10])[CH:12]=[CH2:13])[CH3:16]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 231092-Bromo-4-methylphenolHCID 5447013-Methyl-4-penten-2-olHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 867108152-Bromo-4-methyl-1-((3-methylpent-4-en-2-yl)oxy)benzeneAusbeute 59,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-4-methylphenol (1 g, 5.35 mmol) and 3-methylpent-4-en-2-ol (2.68 g, 26.7 mmol) in THF (20 mL) was added Ph3P (7.01 g, 26.7 mmol) followed by DEAD (4.23 mL, 26.7 mmol) and the resulting mixture was stirred at room temp for 16 h. Water was then added and the mixture was extracted with ether (2×50 mL), dried (Na2SO4), filtered and concentrated. The residue was then purified by Biotage (0-20% EtOAc/hexane) to afford 2-bromo-4-methyl-1-((3-methylpent-4-en-2-yl)oxy)benzene (860 mg, 3.19 mmol, 59.8% yield) as yellow oil. Product is approx 2:1 mixture of trans/cis isomers. 1H NMR (400 MHz, CDCl3) δ 7.38 (d, J=2.0 Hz, 1H), 7.08-7.01 (m, 1H), 6.83-6.79 (m, 1H), 6.02-5.89 (m, 1H), 5.16 (q, J=1.8 Hz, 0.5H), 5.14-5.08 (m, 1.5H), 4.31-4.37 (m, 0.3H), 4.28-4.19 (m, 0.7H), 2.64-2.50 (m, 1H), 2.29 (s, 3H), 1.30-1.24 (m, 3H), 1.19-1.14 (m, 3H).

Aufarbeitung

  1. extractionthe mixture was extracted with ether (2×50 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was then purified by Biotage (0-20% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8e105f46896141aeb7dfda9e017486b6
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906929B2

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