p-Tolyl methyl sulfone → 2-Bromo-4-(methanesulfonyl)-1-methylbenzene

HRID 2357667ノート

反応式

HRID 2357667 の反応式
[Br:1]Br.[C:3]1([CH3:13])[CH:8]=[CH:7][C:6]([S:9]([CH3:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>[Fe].C(OCC)(=O)C>[Br:1][C:8]1[CH:7]=[C:6]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[CH:4][C:3]=1[CH3:13]

参加物

6

反応物 3

HCID 18521p-Tolyl methyl sulfoneHCID 24408BromineHCID 24477Sodium Thiosulfate

生成物 1

HCID 532169872-Bromo-4-(methanesulfonyl)-1-methylbenzene収率 75.1%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of iron powder (0.0669 g, 1.20 mmol) in bromine (2.05 mL, 39.9 mmol) at 0° C. was added methyl p-tolyl sulfone (0.340 g, 2.00 mmol). The reaction was warmed up to RT and stirred for 2 h. The mixture was poured into an ice-cold 1 M solution of sodium thiosulfate and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate (3×). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give 545 mg of crude material. The crude material was purified by column chromatography (3/1 Hex/ethyl acetate to 1/1 ethyl acetate/hexanes) to give 374 mg of 2-bromo-1-methyl-4-(methylsulfonyl)benzene as a white solid. ES+=251.0 (M+H)

後処理

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give 545 mg of crude material
  7. customThe crude material was purified by column chromatography (3/1 Hex/ethyl acetate to 1/1 ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-ccfecc2491fa430cb8ec2a37f7d28238
出典データセット
uspto-grants-2010_07
特許番号
US07759337B2

反応ノート

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