Carbon tetrabromide → Methyl 2-(bromoethyl)-4,5-dichlorobenzoate

HRID 1886468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1886468
[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:13]O)[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:34](Br)(Br)(Br)[Br:35]>C(Cl)Cl>[Br:35][CH2:34][CH2:13][C:4]1[CH:3]=[C:2]([Cl:1])[C:11]([Cl:12])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19804259Methyl-4,5-dichloro-2-(hydroxymethyl)benzoate

Produkt 1

HCID 54367766Methyl 2-(bromoethyl)-4,5-dichlorobenzoateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 169 mg (0.72 mmol) of the product of Step B in 3 mL of CH2Cl2 at 0° C. was added 283 mg (1.08 mmol, 1.5 eq) of triphenylphosphine and 360 mg (1.08 mmol, 1.5 eq) of carbon tetrabromide. The mixture was stirred for 16 hours and quenched with methanol. The reaction was concentrated in vacuo and the resultant oil was flash chromatographed with 2:1 hexane/ethyl acetate to afford the titled compound (107 mg, 50%) as a brownish orange oil.

Aufarbeitung

  1. customquenched with methanol
  2. concentrationThe reaction was concentrated in vacuo
  3. customchromatographed with 2:1 hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8ac58a5aa0614d6cbb5a5a807adfe92d
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05151435

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