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

HRID 42640노트

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HRID 42640 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-983ebd0c0ebc4d28820d26ad5f153b3f
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536203B2

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