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

HRID 61990ノート

反応式

HRID 61990 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-181610ddffee404cb7eb0ee956d975a7
出典データセット
uspto-grants-2016_09
特許番号
US09446012B2

反応ノート

読み込み中…