Phosphorus oxybromide → 1-Bromo-6-(2-ethyl-6-methyl-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

HRID 2077179ノート

反応式

HRID 2077179 の反応式
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](O)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:27][CH3:28])=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].P(Br)(Br)([Br:32])=O>CC#N>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Br:32])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:27][CH3:28])=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

参加物

4

反応物 2

HCID 24613Phosphorus oxybromideHCID 178450851HCID 178450851、化合物

生成物 1

HCID 866170731-Bromo-6-(2-ethyl-6-methyl-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester収率 34.7%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 6-(2-Ethyl-6-methyl-phenoxy)-1,4-dihydroxy-isoquinoline-3-carboxylic acid butyl ester (2.83 mmol, 1.12 g), POBr3 (11 mmol, 3.19 g), MeCN (20 mL) was refluxed gently with stirring for 1 h before it was concentrated in vacuo. The residue was dissolved in CHCl3 (50 mL). Water (10 mL) and subsequently small portions of NaHCO3 (6 g) were added with stirring. The mixture was stirred for 30 min at ambient temperature before it was filtered through a pad of celite. The filtrate was dried over MgSO4. Concentration and purification of the residue by flash column chromatography on silica gel using CH2Cl2 as the eluent gave the title compound as a tan oil (450 mg); MS-(+)-ion: M+1, 79Br/81Br=458.4 and 460.6.

後処理

  1. temperaturewas refluxed gently
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe residue was dissolved in CHCl3 (50 mL)
  4. additionWater (10 mL) and subsequently small portions of NaHCO3 (6 g) were added
  5. stirringwith stirring
  6. stirringThe mixture was stirred for 30 min at ambient temperature before it
  7. filtrationwas filtered through a pad of celite
  8. dry with materialThe filtrate was dried over MgSO4
  9. concentrationConcentration and purification of the residue by flash column chromatography on silica gel

出典と根拠

ORDレコード
ord-e889e5fb73664cae893376f6216194da
出典データセット
uspto-grants-2011_04
特許番号
US07928120B2

反応ノート

読み込み中…