Trifluoroacetic acid → 1-Benzyl-3-bromobenzene

HRID 229370

Reaktionsgleichung

Reaktionsgleichung von HRID 229370
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=1)[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O.[BH4-].[Na+].[OH-].[Na+]>C(Cl)Cl>[CH2:12]([C:11]1[CH:20]=[CH:21][CH:22]=[C:9]([Br:8])[CH:10]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 705483-BromobenzophenoneHCID 4311764Sodium borohydride

Produkt 1

HCID 5975321-Benzyl-3-bromobenzeneAusbeute 92,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, into a cold (10° C.) solution of trifluoroacetic acid (240 mL) was added a solution of 3-bromobenzophenone (11 g, 42.1 mmol) in CH2Cl2 (120 mL) over 10 minutes, followed by slow addition of NaBH4-pellets (19 g) over 1 hour. The reaction mixture was stirred at room temperature for 18 h, poured into ice, basified with NaOH (50%) to pH 8 and extracted with ether. The organic extracts were combined, dried over MgSO4, treated with charcoal and filtered. The filtrate was concentrated in vacuo to give 1-benzyl-3-bromobenzene as an oil (9.65 g, 92% yield) MS m/e (M+H)+ 248; 1H NMR (400 MHZ, DMSOd6) δ 3.89 (s, 2H,), 7.19-7.39 (m, 9H).

Aufarbeitung

  1. additionpoured into ice
  2. extractionextracted with ether
  3. dry with materialdried over MgSO4
  4. additiontreated with charcoal
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d2442339c33a4387b78e5c439d9e60e7
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563796B2

Verknüpfte Notizen

Wird geladen…