Hydrochloric Acid → (2-Fluoro-5-trifluoromethoxyphenyl)pyridin-2-ylmethanol

HRID 593380Notes

Reaction equation

HRID 593380 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Mg]Br)(C)C.[F:13][C:14]1[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][C:15]=1[CH:16]=[O:17].Cl>O1CCCC1.O>[F:13][C:14]1[CH:21]=[CH:20][C:19]([O:22][C:23]([F:25])([F:26])[F:24])=[CH:18][C:15]=1[CH:16]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)[OH:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 79732-BromopyridineHCID 27833242-Fluoro-5-(trifluoromethoxy)benzaldehydeHCID 178418365HCID 178418365, compound

Product 1

HCID 86703870(2-Fluoro-5-trifluoromethoxyphenyl)pyridin-2-ylmethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-bromopyridine (380 mg) in anhydrous tetrahydrofuran (3 mL) is slowly added a 1M solution of isopropylmagnesium bromide in tetrahydrofuran (2.64 mL) at room temperature. After stirring for 2 hours, 2-fluoro-5-(trifluoromethoxy)benzaldehyde (0.50 mL) is added and the reaction mixture stirred for 2 hours. After hydrolysis with water and 3N hydrochloric acid, the mixture is washed with diethyl ether, basified with concentrated sodium hydroxide and extracted with ethyl acetate twice. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography over silica gel (heptane/ethyl acetate 2/1) to afford (2-fluoro-5-trifluoromethoxyphenyl)pyridin-2-ylmethanol as an orange oil.

Workup

  1. stirringthe reaction mixture stirred for 2 hours
  2. washthe mixture is washed with diethyl ether
  3. extractionextracted with ethyl acetate twice
  4. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by chromatography over silica gel (heptane/ethyl acetate 2/1)

Sources & evidence

ORD record
ord-ff42c90ccea043e58fd1574e4d789b05
Source dataset
uspto-grants-2016_01
Patent number
US09242959B2

Reaction notes

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