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

HRID 2095626ノート

反応式

HRID 2095626 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 670043632-Chloro-4-difluoromethoxy-3-dimethoxymethyl-1-fluorobenzene収率 63%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-365a7249b7d442c28fbfdb955b56bb05
出典データセット
uspto-grants-2013_05
特許番号
US08445510B2

反応ノート

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