Hydrogen Bromide → 6-Bromo-1-tetralone

HRID 63612

Reaktionsgleichung

Reaktionsgleichung von HRID 63612
N([O-])=O.[Na+].N[C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10][CH2:9]2.[BrH:17]>O>[Br:17][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10][CH2:9]2

Komponenten

5

Edukt 3

HCID 260Hydrogen Bromide2×HCID 3395376-Amino-1,2,3,4-tetrahydronaphthalen-1-oneHCID 23668193Sodium Nitrite

Produkt 1

HCID 101050696-Bromo-1-tetraloneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of NaNO2 (2.35 g, 34 mmol) in water (10 mL) was added dropwise to the solution of 6-amino-1,2,3,4-tetrahydronaphthalen-1-one (5.0 g, 31 mmol) in 25% HBr (16 mL) at 0° C. The suspension was then transferred to a stirred mixture of CuBr (8.9 g, 62 mmol) in 48% HBr (30 mL) at 0° C. The resulting mixture was allowed to warm to rt and stirred for 1 h. The mixture was extracted with EtOAc, dried (Na2SO4), and concentrated. The residue was purified by silica gel chromatography (0%-60% EtOAc/Hex) to give 5.6 g (80%) of the title compound as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 2.10-2.16 (2H, m), 2.64 (2H, t, J=6.4 Hz), 2.94 (2H, t, J=6.0 Hz), 7.42 (1H, s), 7.44 (1H, s), 7.87 (1H, d, J=8.9 Hz). [M+H] calc'd for C10H9BrO, 225, 227. found 225, 227.

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (0%-60% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-60fe536885a24b3ebd69d37f8cb27bf5
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447046B2

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