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

HRID 529736

반응식

HRID 529736 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)benzene

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 DMF (25 mL) was added sodium chlorodifluoroacetate (8.42 g, 55.2 mmol), cesium carbonate (10.97 g, 33.67 mmol) and water (2.5 mL). The reaction was stirred at 100° C. for 16 hours. The reaction mixture was partitioned between ethyl acetate and water, the organic portion washed with brine, dried (MgSO4), and evaporated. The crude product was purified by flash chromatography on silica eluting with 0-20% EtOAc in heptanes to yield 2-bromo-4-chloro-1-(difluoromethoxy)benzene as a clear, colorless oil (2.98 g, 48%). LCMS (ESI) no m/z signal; 1H NMR (400 MHz, DMSO-d6) δ: (ppm) 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 (MgSO4)
  4. customevaporated
  5. customThe crude product was purified by flash chromatography on silica eluting with 0-20% EtOAc in heptanes

출처 및 근거

ORD 기록
ord-7ada66305a5f4875ac2c1ab615adcd16
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346815B2

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