Triphenylphosphine → 4-Bromomethyl-2-(3-chloro-phenoxy)-1-methoxy-benzene

HRID 332576

Reaktionsgleichung

Reaktionsgleichung von HRID 332576
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][C:6]1[CH:7]=[C:8]([CH2:14]O)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C(=O)N([Br:45])C(=O)C1>C(Cl)Cl>[Br:45][CH2:14][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:6]([O:5][C:4]2[CH:16]=[CH:17][CH:18]=[C:2]([Cl:1])[CH:3]=2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 57701122[3-(3-Chloro-phenoxy)-4-methoxy-phenyl]-methanol

Produkt 1

HCID 577011304-Bromomethyl-2-(3-chloro-phenoxy)-1-methoxy-benzeneAusbeute 91,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3-(3-chloro-phenoxy)-4-methoxy-phenyl]-methanol (13) (315 mg, 1.2 mmol) and triphenylphosphine (390 mg, 1.5 mmol) in methylene chloride (5 ml) was added NBS (0.250 mg, 1.4 mmol) in portions at 0° C. under nitrogen. After 10 min of stirring at 0° C., the mixture was allowed to warm to room temperature, and continued to stir for 16 h. After the solvent was removed, the residue was purified by silica gel column chromatography with ether/hexane as eluent to give 360 mg (85% yield) of product (14).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringto stir for 16 h
  3. customAfter the solvent was removed
  4. customthe residue was purified by silica gel column chromatography with ether/hexane as eluent

Quellen und Nachweise

ORD-Eintrag
ord-8c044c98209c4847b1ab1c78200d10ff
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877816B2

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