Dimethyl Sulfoxide → 1-[4-(2-Bromoethyl)phenyl]-5-phenylpentan-1-one

HRID 1795705Notes

Reaction equation

HRID 1795705 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Br:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([OH:31])[CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl>[Br:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:31])[CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 221784871-[4-(2-Bromoethyl)phenyl]-5-phenylpentan-1-ol

Product 1

HCID 221784791-[4-(2-Bromoethyl)phenyl]-5-phenylpentan-1-oneYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of dimethyl sulfoxide (12. 7 ml) in methylene chloride (320 ml) was added a solution of oxalyl chloride (7.7 ml) in methylene chloride (320 ml) over 10 minutes under a nitrogen atmosphere at −68 to −65° C., and the mixture was stirred at the said temperature for 10 minutes. Then, a solution of 1-[4-(2-bromoethyl)phenyl]-5-phenylpentan-1-ol (20.7 g) in methylene chloride (80 ml) was added thereto at −68 to −65° C. over 20 minutes and the mixture was stirred at the said temperature for an hour. Triethylamine (41.6 ml) was further added thereto over 10 minutes at the said temperature and the mixture was stirred for 2.5 hours while raising the temperature of the mixture to 0° C. gradually. The reaction mixture was washed with water (100 ml) and saturated brine (100 ml), dried over anhydrous sodium sulfate and the solvent was distilled away under reduced pressure to give a brown oily substance. The obtained brown oily substance was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=20:1) to give 1-[4-(2-bromoethyl)phenyl]-5-phenylpentan-1-one (18.2 g) as a yellow oily substance.

Workup

  1. waitat −68 to −65° C. over 20 minutes
  2. stirringthe mixture was stirred at the said temperature for an hour
  3. waitover 10 minutes at the said temperature
  4. stirringthe mixture was stirred for 2.5 hours
  5. washThe reaction mixture was washed with water (100 ml) and saturated brine (100 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled away under reduced pressure
  8. customto give a brown oily substance
  9. customThe obtained brown oily substance was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-5e260467101c42cf8279ef57bd2c7340
Source dataset
uspto-grants-2006_04
Patent number
USRE039072E1

Reaction notes

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