Bromine → 1-(5-Bromo-3-(trifluoromethyl)pyridin-2-yl)ethanol

HRID 545087Notes

Reaction equation

HRID 545087 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[C:4]([CH:9]([OH:11])[CH3:10])=[N:5][CH:6]=[CH:7][CH:8]=1.[Br:14]Br>CO>[Br:14][C:7]1[CH:8]=[C:3]([C:2]([F:1])([F:12])[F:13])[C:4]([CH:9]([OH:11])[CH3:10])=[N:5][CH:6]=1

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 671892191-(3-(Trifluoromethyl)pyridin-2-yl)ethanol

Product 1

HCID 671904531-(5-Bromo-3-(trifluoromethyl)pyridin-2-yl)ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 1-(3-(trifluoromethyl)pyridin-2-yl)ethanol (8.8 g, 0.046 moles) in anhydrous MeOH (80 mL) and add bromine (2.35 mL) dropwise at room temperature. Reflux the mixture under N2 atmosphere for 3 weeks with the addition of bromine (1.0 mL) on each day. Concentrate the reaction mixture under vacuum, dilute with water (100 mL), neutralize with NaHCO3, extract with EtOAc (3×100 mL) and dry (MgSO4). Filter the dried extract and concentrate under vacuum to afford a yellow oil. Purify the crude product by column chromatography to afford the title compound as a pale yellow oil.

Workup

  1. temperatureReflux the mixture under N2 atmosphere for 3 weeks
  2. concentrationConcentrate the reaction mixture under vacuum
  3. additiondilute with water (100 mL)
  4. extractionextract with EtOAc (3×100 mL)
  5. dry with materialdry (MgSO4)
  6. filtrationFilter the dried
  7. extractionextract
  8. concentrationconcentrate under vacuum
  9. customto afford a yellow oil
  10. customPurify the crude product by column chromatography

Sources & evidence

ORD record
ord-5570b20951ca44dfbb6b189522bad0a0
Source dataset
uspto-grants-2011_05
Patent number
US07935702B2

Reaction notes

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