Acetic Acid → (4-Hydroxy-3-methoxyphenyl)(2-(trifluoromethyl)pyridin-3-yl)methanone

HRID 61990Notes

Reaction equation

HRID 61990 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[C:18]([C:23]([F:26])([F:25])[F:24])=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:16])=[CH:11][C:10]=1[O:27][CH3:28])C1C=CC=CC=1.Br.C(O)(=O)C>ClCCl>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[C:18]([C:23]([F:24])([F:25])[F:26])=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:16])=[CH:11][C:10]=1[O:27][CH3:28]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 67037150(4-Benzyloxy-3-methoxy-phenyl)-(2-trifluoromethyl-pyridin-3-yl)-methanone

Product 1

HCID 68703345(4-Hydroxy-3-methoxyphenyl)(2-(trifluoromethyl)pyridin-3-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-benzyloxy-3-methoxy-phenyl)-(2-trifluoromethyl-pyridin-3-yl)-methanone (0.913 g, 2.36 mmol) in dichloromethane cooled in an ice-water bath was added a 30% solution of hydrogen bromide in acetic acid (3.54 mL, 17.7 mmol) dropwise. The resulting solution was allowed to stir at room temperature overnight then poured onto ice-water (100 mL). The phases were separated and the aqueous phase extracted with dichloromethane (10 mL). The combined organic layers were washed with water and brine, then dried over anhydrous sodium sulphate and filtered. Evaporation of the solvent left a brown oil that was chromatographed over silica gel (petroleum ether/ethyl acetate, 1:1) to give (4-hydroxy-3-methoxyphenyl)(2-(trifluoromethyl)pyridin-3-yl)methanone as a colourless solid, 0.561 g (80%).

Workup

  1. additionthen poured onto ice-water (100 mL)
  2. customThe phases were separated
  3. extractionthe aqueous phase extracted with dichloromethane (10 mL)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customEvaporation of the solvent
  8. waitleft a brown oil that
  9. customwas chromatographed over silica gel (petroleum ether/ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-181610ddffee404cb7eb0ee956d975a7
Source dataset
uspto-grants-2016_09
Patent number
US09446012B2

Reaction notes

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