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

HRID 2357667노트

반응식

HRID 2357667 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 532169872-Bromo-4-(methanesulfonyl)-1-methylbenzene수율 75.1%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 8857Ethyl Acetate용매

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-ccfecc2491fa430cb8ec2a37f7d28238
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07759337B2

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