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

HRID 1429264Notes

Reaction equation

HRID 1429264 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-72cf5e69d516464e8e8991bbdf91234f
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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