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

HRID 30600

反応式

HRID 30600 の反応式
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]

参加物

7

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ad138f9c0f41405a9be1bd18bbb6fdde
出典データセット
uspto-grants-2008_09
特許番号
US07423158B2

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