Triphenylphosphine → 5-(3-(Bromomethyl)-4-methoxyphenyl)-2-methyl-2H-tetrazole

HRID 391389Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 391389
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[N:11][N:12]([CH3:14])[N:13]=2)=[CH:5][C:4]=1[CH2:15]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:36]N1C(=O)CCC1=O>C(Cl)Cl>[Br:36][CH2:15][C:4]1[CH:5]=[C:6]([C:9]2[N:10]=[N:11][N:12]([CH3:14])[N:13]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 58993522(2-Methoxy-5-(2-methyl-2H-tetrazol-5-yl)phenyl)methanol

Produkt 1

HCID 589936045-(3-(Bromomethyl)-4-methoxyphenyl)-2-methyl-2H-tetrazoleAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(2-Methoxy-5-(2-methyl-2H-tetrazol-5-yl)phenyl)methanol (100 mg, 0.45 mmol) and triphenylphosphine (238 mg, 0.9 mmol) were combined in methylene chloride (3 mL) and cooled to 0° C. N-Bromosuccinimide (170 mg, 0.95 mmol) was introduced in portions and the reaction allowed to warm to room temperature. After 16 h, the reaction mixture was diluted with methylene chloride and washed with concentrated sodium bicarbonate (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (30% ethyl acetate/hexanes) gave 80 mg (63%) of the desired material. LC/MS (HPLC method 3): tR=2.69 min, 285.02 (MH)+.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. washwashed with concentrated sodium bicarbonate (2×), brine (2×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3bb644a6e2f64e0b8eb9590f31294264
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383821B2

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