Bromide ion → 3-Bromo-1h-indole

HRID 278396ノート

反応式

HRID 278396 の反応式
[Br-:1].COC1C=CC(C(O)C2C=CC(OC)=CC=2)=CC=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23](S(O)(=O)=O)=[CH:22][CH:21]=1.C[N:32]1[CH2:36]CCC1=O>C1C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:30]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:32][CH:36]=1

参加物

7

反応物 4

HCID 259Bromide ionHCID 6101p-Toluenesulfonic acidHCID 13387N-methyl-2-pyrrolidoneHCID 69768p,p'-Dimethoxybenzhydryl alcohol

生成物 1

HCID 27632773-Bromo-1h-indole収率 87%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of the above bromide (1.09 g, 2.8 mmol) in benzene (60 mL) and N-methylpyrrolidinone (6 mL) was added 4,4′-dimethoxybenzhydrol (818 mg, 3.4 mmol) and p-toluenesulfonic acid (532 mg, 2.8 mmol), and the mixture was heated to reflux. After 24 hours the reaction was cooled to room temperature and diluted with ethyl acetate (200 mL). The organic layer was washed with NaHCO3 (2×), H2O (2×), and brine(2×). The organic layer was dried over anhydrous MgSO4, filtered and solvent was removed in vacuo. The crude material was purified via column chromatography (10% EtOAc-hexane) to provide the desired DMB protected 3-bromo indole derivative (1.5 g, 2.4 mmol, 87% yield) as an orange solid: (MS m/z (M+H) 615, 617).

後処理

  1. temperaturethe mixture was heated to reflux
  2. washThe organic layer was washed with NaHCO3 (2×), H2O (2×), and brine(2×)
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customsolvent was removed in vacuo
  6. customThe crude material was purified via column chromatography (10% EtOAc-hexane)
  7. customto provide the desired DMB

出典と根拠

ORDレコード
ord-9bd2e99fc12a412c8570c5e815271937
出典データセット
uspto-grants-2002_03
特許番号
US06359130B1

反応ノート

読み込み中…