N-bromobutanimide → 1-Acetyl-8-bromo-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1741045ノート

反応式

HRID 1741045 の反応式
[C:1]([N:4]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[CH2:8][CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Br:16]N1C(=O)CCC1=O>CC(O)=O.C(OCC)(=O)C>[C:1]([N:4]1[C:10]2[CH:11]=[C:12]([Br:16])[C:13]([OH:15])=[CH:14][C:9]=2[CH2:8][CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 218338251-Acetyl-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepine

生成物 1

HCID 218338021-Acetyl-8-bromo-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepine収率 31%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1-Acetyl-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepine (D24, 2.81 g, 14 mmol) was stirred in glacial AcOH (50 ml) as N-bromosuccinimide (2.69 g, 15 mmol) was added portionwise over 20 min. The mixture was stirred for 30 min, diluted with ethyl acetate (500 ml), washed with water, K2CO3 solution and brine, dried (Na2SO4) and evaporated to give a tan solid, shown by NMR and TLC to be a mixture of dibromo and mono-bromo isomers. Chromatography on silica, eluting with 0-25% ethyl acetate/dichloromethane, yielded pure title compound (1.22 g, 31%) as a cream solid.

後処理

  1. additionwas added portionwise over 20 min
  2. washwashed with water, K2CO3 solution and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customto give a tan solid
  6. additiona mixture of dibromo and mono-bromo isomers
  7. washChromatography on silica, eluting with 0-25% ethyl acetate/dichloromethane

出典と根拠

ORDレコード
ord-7346bbfc15064b649313c71b761e3bb1
出典データセット
uspto-grants-1999_10
特許番号
US05972951

反応ノート

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