Water → 2-Chloro-4-difluoromethoxy-3-dimethoxymethyl-1-fluorobenzene

HRID 2095626노트

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HRID 2095626 반응식
[Cl:1][C:2]1[C:3]([CH:10]([O:13][CH3:14])[O:11][CH3:12])=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].Cl[C:16]([F:21])([F:20])C([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH:10]([O:13][CH3:14])[O:11][CH3:12])=[C:4]([O:9][CH:16]([F:21])[F:20])[CH:5]=[CH:6][C:7]=1[F:8]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2734985Sodium chlorodifluoroacetateHCID 670040603-Chloro-2-dimethoxymethyl-4-fluorophenol

생성물 1

HCID 670043632-Chloro-4-difluoromethoxy-3-dimethoxymethyl-1-fluorobenzene수율 63%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

In a single neck flask, 3-chloro-2-dimethoxymethyl-4-fluorophenol (22 g, 100 mmol), sodium chlorodifluoroactate (30.3 g, 200 mmol) and potassium carbonate (27.5 g, 200 mmol) were taken up in DMF (145 mL) under nitrogen atmosphere and heated at 90° C. for 16 h. The reaction mixture was cooled to room temperature, poured into water and extracted with ethyl acetate (2×200 mL, 100 mL). The combined organic layers were washed with water, dried over sodium sulfate, filtered and concentrated to give crude product, which was purified by column chromatography on silica gel using 10% ethyl acetate in hexane as an eluent to give 17 g (63% yield) of the title compound. 1H NMR (CDCl3, 300 MHz): δ=7.11-7.13 (m, 2H), 6.45 (t, J=75 Hz, 1H), 5.70 (s, 1H), 3.46 (s, 6H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (2×200 mL, 100 mL)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give crude product, which
  8. customwas purified by column chromatography on silica gel using 10% ethyl acetate in hexane as an eluent

출처 및 근거

ORD 기록
ord-365a7249b7d442c28fbfdb955b56bb05
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445510B2

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