Methyl iodide → 1,2,4-Trifluoro-5-(methylsulfonyl)benzene

HRID 407870

반응식

HRID 407870 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[S:10]([OH:12])=[O:11].IC.[CH2:15](N(C(C)C)C(C)C)C>CN(C=O)C>[F:9][C:5]1[CH:4]=[C:3]([S:10]([CH3:15])(=[O:12])=[O:11])[C:2]([F:1])=[CH:7][C:6]=1[F:8]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 572413752,4,5-Trifluorobenzenesulfinic acid

생성물 1

HCID 467393961,2,4-Trifluoro-5-(methylsulfonyl)benzene수율 71.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2,4,5-trifluorobenzenesulfinic acid (34 g, 173 mmol), in DMF (200 mL), was added iodomethane (21.6 mL, 347 mmol), and N-ethyl-N-isopropylpropan-2-amine (60.5 mL, 347 mmol). The reaction mixture was stirred overnight at ambient temperature. The reaction was concentrated and partitioned between water and ethyl acetate and extracted with CH2Cl2. The combined organic layers were concentrated and purified over silica gel (15-100% EtOAc in hexanes) to afford 1,2,4-trifluoro-5-(methylsulfonyl)benzene (25.8 g, 123 mmol, 71% yield) as yellow solid.

후처리

  1. concentrationThe reaction was concentrated
  2. custompartitioned between water and ethyl acetate
  3. extractionextracted with CH2Cl2
  4. concentrationThe combined organic layers were concentrated
  5. custompurified over silica gel (15-100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-4d3484d721434e5da22963726d069d9d
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754226B2

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