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

HRID 1952332Notes

Reaction equation

HRID 1952332 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-de97117fb1374d3791227940c718b3c7
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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