Acetone → (R)-2-fluoro-2-(3-bromophenyl)acetaldehyde

HRID 30600

Reaktionsgleichung

Reaktionsgleichung von HRID 30600
C([C@H]1NC(C)(C)N(C)C1=O)C1C=CC=CC=1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:27])(=O)=O)=CC=1.CC(C)=O.[Br:41][C:42]1[CH:43]=[C:44]([CH2:48][CH:49]=[O:50])[CH:45]=[CH:46][CH:47]=1>CCOCC.C(O)(C)C>[F:27][C@H:48]([C:44]1[CH:45]=[CH:46][CH:47]=[C:42]([Br:41])[CH:43]=1)[CH:49]=[O:50]

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 588007N-FluorobenzenesulfonimideHCID 11184391(5R)-(+)-2,2,3-Trimethyl-5-benzyl-4-imidazolidinoneHCID 20387554(3-Bromophenyl)acetaldehyde

Produkt 1

HCID 86611665(R)-2-fluoro-2-(3-bromophenyl)acetaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A homogeneous mixture of (5R)-5-benzyl-2,2,3-trimethyl imidazolidin-4-one dichloroaccetic acid salt (97 mg, 0.4 mmol) and N-fluorobenzenesulfonimide (3.15 g, 10 mmol) in a 9:1 mixture of acetone and isopropanol at room temperature is treated with (3-bromophenyl)acetaldehyde (280 mg, 1.4 mmol), stirred for 1 h at room temperature, cooled to −78° C., diluted with ether, and filtered through a pad of celite. The filtercake is washed with additional ether. The combined filtrates are treated with methylsulfide (5 mL), washed with saturated NaHCO3 and brine, dried over MgSO4 and concentrated under reduced pressure to give (R)-2-fluro-2-(3-bromophenyl)acetaldehyde.

Aufarbeitung

  1. temperaturecooled to −78° C.
  2. filtrationfiltered through a pad of celite
  3. washThe filtercake is washed with additional ether
  4. additionThe combined filtrates are treated with methylsulfide (5 mL)
  5. washwashed with saturated NaHCO3 and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ad138f9c0f41405a9be1bd18bbb6fdde
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423158B2

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