Benzoyl Peroxide → 2-bromo-1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one O-methyl-oxime

HRID 719125Notes

Reaction equation

HRID 719125 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[CH2:5][CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[Br:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][N:3]=[C:4]([C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)[CH:5]([Br:19])[CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 738525441-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one O-methyl-oxime

Product 1

HCID 738525452-bromo-1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one O-methyl-oximeYield 80%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one O-methyl-oxime (1.120 g, 4.214 mmol) in carbon tetrachloride were added N-bromosuccinimide (812 mg, 4.425 mmol) and benzoyl peroxide (102 mg, 0.4 mmol). The resulting mixture was heated at reflux for 12 h. Upon cooling to room temperature, the solids were filtered and washed with diethyl ether. The filtrate was washed with aqueous solution of sodium bicarbonate, sodium thiosulfate and brine. It was then dried with anhydrous sodium sulfate and concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32–63 μm, 60 Å silica gel) eluting with 1–2% ethyl acetate in hexanes yielded 2-bromo-1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one O-methyl-oxime (1.16 g, 80%) as yellow oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 12 h
  3. filtrationthe solids were filtered
  4. washwashed with diethyl ether
  5. washThe filtrate was washed with aqueous solution of sodium bicarbonate, sodium thiosulfate and brine
  6. dry with materialIt was then dried with anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32–63 μm, 60 Å silica gel)
  9. washeluting with 1–2% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d099b848a5c6466c850a0ea8c2f83cdf
Source dataset
uspto-grants-2006_11
Patent number
US07132421B2

Reaction notes

Loading…