Carbon tetrabromide → 4-(Bromomethyl)-2,6-dimethylphenyl acetate

HRID 43290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 43290
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH2:12]O)=[CH:7][C:6]=1[CH3:14])(=[O:3])[CH3:2].[Br:15]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH2:12][Br:15])=[CH:7][C:6]=1[CH3:14])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 280655654-(Hydroxymethyl)-2,6-dimethylphenyl acetate

Produkt 1

HCID 132969354-(Bromomethyl)-2,6-dimethylphenyl acetateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of commercially available 4-(hydroxymethyl)-2,6-dimethylphenyl acetate (1 g, 5.15 mmol) and perbromomethane (2.39 g, 7.21 mmol) in tetrahydrofuran (25 mL) was added triphenylphosphine (1.620 g, 6.18 mmol). The mixture was stirred at room temperature for 6 hours then concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, hexane:ethyl acetate 4:1) to provide the title compound (1.05 g, 80% yield). MS (DCI/NH3) m/z 274 (M+NH4)+.

Aufarbeitung

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography (silica gel, hexane:ethyl acetate 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-316f60850f8944f7a843c8241538bade
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536336B2

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