Triphenylphosphine → Phosphonium, [[3-(methoxycarbonyl)phenyl]methyl]triphenyl-, bromide

HRID 223767

Reaktionsgleichung

Reaktionsgleichung von HRID 223767
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH2:11][Br:12])[CH:8]=[CH:9][CH:10]=1)=[O:4].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1C=CC=CC=1>[Br-:12].[C:3]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[CH2:11][P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([O:2][CH3:1])=[O:4]

Komponenten

4

Edukt 2

HCID 11776TriphenylphosphineHCID 517981Methyl 3-(bromomethyl)benzoate

Produkt 1

HCID 10051285Phosphonium, [[3-(methoxycarbonyl)phenyl]methyl]triphenyl-, bromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of 230 g (1.0 mole) of methyl-α-bromo-m-toluate and 300 g (1.2 mole) of triphenyl phosphine in 1 l of dry benzene was refluxed for 2 hr. After 15 minutes, the phosphonium bromide started precipitating from the solution. After cooling the flask to room temperature, the solid was filtered, washed with plenty of petroleum ether and dried. The yield 487 g was quantitative. m.p. 234°-236° C. The infrared spectrum showed absorption of 1720 cm-1 (COOCH3). NMR (CDCl3) showed 3.8 (S, --COOCH3, 3), 5.5-5.8 (d, --CH2 -P, 2), and 7-8.4 (m, aromatic, 19). Anal. calcd. for C27H24O2P Br: C, 65.98%, H, 4.88%, Br. 16.29%. Found: C, 65.88%, H, 4.82%, Br, 16.49%.

Aufarbeitung

  1. temperaturewas refluxed for 2 hr
  2. customthe phosphonium bromide started precipitating from the solution
  3. filtrationthe solid was filtered
  4. washwashed with plenty of petroleum ether
  5. customdried
  6. customabsorption of 1720 cm-1 (COOCH3)

Quellen und Nachweise

ORD-Eintrag
ord-987b5be7905646a38caa4a2b0300121a
Quelldatensatz
uspto-grants-1982_10
Patentnummer
US04356292

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