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

HRID 719125ノート

反応式

HRID 719125 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d099b848a5c6466c850a0ea8c2f83cdf
出典データセット
uspto-grants-2006_11
特許番号
US07132421B2

反応ノート

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