Water → 2-Bromo-4-chloro-1-(difluoromethoxy)benzene

HRID 1466586

반응식

HRID 1466586 반응식
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].Cl[C:11]([F:16])([F:15])C([O-])=O.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][CH:11]([F:16])[F:15]

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 696702-Bromo-4-chlorophenolHCID 2734985Sodium chlorodifluoroacetate

생성물 1

HCID 463115372-Bromo-4-chloro-1-(difluoromethoxy)benzene수율 48.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a solution of 2-bromo-4-chlorophenol (4.98 g, 24.0 mmol) in 25 mL DMF was added sodium chlorodifluoroacetate (8.42 g, 55.2 mmol), cesium carbonate (10.97 g, 33.67 mmol) and 2.5 mL water. The reaction was stirred at 100° C. for 16 hours. The reaction mixture was partitioned between ethyl acetate and water, and the organic portion washed with brine, dried over magnesium sulfate, and concentrated. The crude product was purified by flash chromatography on silica gel (0 to 20% ethyl acetate in heptanes) to yield 2.98 g (48%) of 2-bromo-4-chloro-1-(difluoromethoxy)benzene as a clear, colorless oil. LCMS (ESI) no m/z signal; 1H NMR (400 MHz, DMSO-d6) δ: 7.90 (d, 1H), 7.54 (dd, 1H), 7.38 (d, 1H), 7.28 (t, 1H).

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washthe organic portion washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography on silica gel (0 to 20% ethyl acetate in heptanes)

출처 및 근거

ORD 기록
ord-df599684ba66488ebcb2d84c403ab2f7
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999998B2

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