Ethanol → 1,3-bis(4-bromophenyl)-2-(4-tert-butylphenyl)-1H-pyrrole

HRID 1411444ノート

反応式

HRID 1411444 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/C=C/C=O)=[CH:4][CH:3]=1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][CH:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=2)[C:21]#N)=[CH:15][CH:14]=1.[OH-].[K+].[CH2:35](O)[CH3:36]>>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:36]=[CH:35][C:21]([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)=[C:20]2[C:23]2[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=2)=[CH:15][CH:14]=1

参加物

5

反応物 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 6285035Trans-4-bromocinnamaldehydeHCID 582268062-(4-Bromophenylamino)-2-(4-tert-butylphenyl)acetonitrile

生成物 1

HCID 582266091,3-bis(4-bromophenyl)-2-(4-tert-butylphenyl)-1H-pyrrole収率 10%

実験手順

To the product of Example 7.1C (0.676 g, 3.2 mmol) and the product from Example 7.1A (1.0 g, 2.91 mmol) was added ethanol (30 mL) followed by potassium hydroxide (0.163 g, 2.91 mmol), and the mixture was stirred at room temperature for 16 hours. Afterwards the mixture was concentrated. The residue was partitioned between water and ethyl acetate. The organic layers were combined, dried and then concentrated. The residue was purified by chromatography (silica gel, hexanes in ethyl acetate) which afforded 150 mg, (10%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.37 (m, 3H), 7.32 (d, J=8.5, 2H), 7.21 (d, J=8.4 Hz, 2H), 7.06 (d, J=8.3 Hz, 2H), 6.93 (m, 4H), 6.51 (dd, J=2.9 Hz, 1H), 1.29 (s, 9H).

後処理

  1. concentrationAfterwards the mixture was concentrated
  2. customThe residue was partitioned between water and ethyl acetate
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (silica gel, hexanes in ethyl acetate) which

出典と根拠

ORDレコード
ord-981882c5583c4f1abee54b6d6969fa56
出典データセット
uspto-grants-2014_12
特許番号
US08921514B2

反応ノート

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