Carbon tetrabromide → 1-Bromo-3-(1-bromoethyl)-5-fluorobenzene

HRID 391428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 391428
[Br:1][C:2]1[CH:3]=[C:4]([CH:9](O)[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1.C(Br)(Br)(Br)[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.CCCCC>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH:9]([Br:13])[CH3:10])[CH:3]=1

Komponenten

6

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 222402011-(3-Bromo-5-fluorophenyl)ethanol

Produkt 1

HCID 589936681-Bromo-3-(1-bromoethyl)-5-fluorobenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8003PentaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (±)-1-(3-bromo-5-fluorophenyl)ethanol (1.0 g, 4.6 mmol) and carbon tetrabromide (1.82 g, 5.48 mmol) in tetrahydrofuran (5 mL) at 0° C. was added triphenylphosphine (1.44 g, 5.48 mmol). The resulting solution was stirred at room temperature for 45 min. The reaction was diluted with several volumes of pentane, and filtered to remove the undissolved solids which were discarded. The organics were concentrated and purified by column chromatography (1% ethyl acetate/hexanes) to give 1.26 g (98%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ 7.35 (s, 1H), 7.17 (m, 1H), 7.09 (m, 1H), 5.06 (q, J=7.0 Hz, 1H), 2.00 (d, J=7.0 Hz, 3H); 13C NMR (126 MHz, CDCl3) δ ppm 163.6, 161.6, 147.2 (m), 126.0 (m), 122.8, 122.7, 119.2, 119.0, 113.3, 113.1, 46.5, 26.7.

Aufarbeitung

  1. filtrationfiltered
  2. customto remove the undissolved solids which
  3. concentrationThe organics were concentrated
  4. custompurified by column chromatography (1% ethyl acetate/hexanes)
  5. customto give 1.26 g (98%) as a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-826719df704b4db38ef3a8d109aa5460
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383821B2

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