Potassium Hydroxide → 3-(3-Bromo-5-chlorophenoxy)-4-(trifluoromethyl)pyridin-2-ol

HRID 1952332ノート

反応式

HRID 1952332 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[O:5][C:6]1[C:7](Cl)=[N:8][CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13].[OH-:21].[K+]>C(O)(C)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[O:5][C:6]1[C:7](=[O:21])[NH:8][CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13]

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 584600423-(3-Bromo-5-chlorophenoxy)-2-chloro-4-(trifluoromethyl)pyridine

生成物 1

HCID 584600533-(3-Bromo-5-chlorophenoxy)-4-(trifluoromethyl)pyridin-2-ol

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

To a round bottom flask charged with 3-(3-bromo-5-chlorophenoxy)-2-chloro-4-(trifluoromethyl)pyridine (9.1 g, 25.3 mmol) and potassium hydroxide (3.96 g, 70.5 mmol) was added tert-butanol (100 mL). This suspension was placed in an oil bath at 75° C. After 48 hours, the reaction mixture was allowed to cool to room temperature and was quenched with saturated aqueous ammonium chloride (50 mL) and diluted with water (50 mL). The mixture was extracted with ethyl acetate (2×100 mL) and the combined organic fractions were washed with water (3×100 mL). The solvent was evaporated under reduced pressure to yield a solid. This was adsorbed onto silica and purified by column chromatography on a pre-packed silica gel Redi Sep 330 gram column, eluting with 0-5% methanol in CH2Cl2 to give the title compound. 1H NMR (DMSO-d6) δ 12.68 (s, 1H), 7.58 (d, J=6.8 Hz, 1H), 7.44-7.40 (m, 1H), 7.20-7.18 (m, 1H), 7.13-7.10 (m, 1H), 6.47 (d, J=6.8 Hz, 1H). FIRMS (M+1)=367.9295.

後処理

  1. customThis suspension was placed in an oil bath at 75° C
  2. customwas quenched with saturated aqueous ammonium chloride (50 mL)
  3. additiondiluted with water (50 mL)
  4. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  5. washthe combined organic fractions were washed with water (3×100 mL)
  6. customThe solvent was evaporated under reduced pressure
  7. customto yield a solid
  8. custompurified by column chromatography on a pre-packed silica gel Redi Sep 330 gram column
  9. washeluting with 0-5% methanol in CH2Cl2

出典と根拠

ORDレコード
ord-de97117fb1374d3791227940c718b3c7
出典データセット
uspto-grants-2013_03
特許番号
US08404856B2

反応ノート

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