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

HRID 30600

Reaction equation

HRID 30600 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ad138f9c0f41405a9be1bd18bbb6fdde
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Linked notes

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