Acetic Acid → 3-Methoxy-3'-(6-(trifluoromethyl)pyridin-2-yl)biphenyl-4-ol

HRID 42640Notes

Reaction equation

HRID 42640 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[N:22]=3)[CH:16]=2)=[CH:11][C:10]=1[O:31][CH3:32])C1C=CC=CC=1.Br.C(O)(=O)C>ClCCl>[CH3:32][O:31][C:10]1[CH:11]=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[N:22]=3)[CH:16]=2)[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 68702253HCID 68702253, compound

Product 1

HCID 687058143-Methoxy-3'-(6-(trifluoromethyl)pyridin-2-yl)biphenyl-4-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4′-(benzyloxy)-3′-methoxybiphenyl-3-yl)-6-(trifluoromethyl)pyridine (1.061 g, 2.44 mmol) in dichloromethane (20 mL) cooled in an ice-water bath was added a 30% solution of hydrogen bromide in acetic acid (4 mL, 20 mmol) dropwise. The resulting solution was allowed to stir at room temperature for six hours then poured onto ice-water (100 mL). The phases were separated and the aqueous phase was 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, 4:1) to give 3-methoxy-3′-(6-(trifluoromethyl)pyridin-2-yl)biphenyl-4-ol as a clear oil, 0.547 g (65%).

Workup

  1. additionthen poured onto ice-water (100 mL)
  2. customThe phases were separated
  3. extractionthe aqueous phase was 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, 4:1)

Sources & evidence

ORD record
ord-983ebd0c0ebc4d28820d26ad5f153b3f
Source dataset
uspto-grants-2013_09
Patent number
US08536203B2

Reaction notes

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