p-Bromobenzenesulfonyl chloride → (E)-3-[1-(4-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester

HRID 2408464Notes

Reaction equation

HRID 2408464 reaction equation
[H-].[Na+].C1COCC1.[C:8]([O:12][C:13](=[O:21])/[CH:14]=[CH:15]/[C:16]1[CH:20]=[CH:19][NH:18][CH:17]=1)([CH3:11])([CH3:10])[CH3:9].[Br:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>O>[C:8]([O:12][C:13](=[O:21])/[CH:14]=[CH:15]/[C:16]1[CH:20]=[CH:19][N:18]([S:29]([C:26]2[CH:27]=[CH:28][C:23]([Br:22])=[CH:24][CH:25]=2)(=[O:31])=[O:30])[CH:17]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 66646340tert-butyl (2E)-3-(1H-pyrrol-3-yl)prop-2-enoate

Product 1

HCID 66646304(E)-3-[1-(4-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-30 °C

Procedure

A mixture of 0.85 g NaH with 70.0 ml THF is cooled to −30° C. and 5.0 g (E)-3-(1H-pyrrol-3-yl)-acrylic acid tert-butyl ester are added. During the addition there is liberated a gas. The solution is stirred at ambient temperature for 0.5 h. Then 7.9 g 4-bromobenzenesulfonylchloride is added by −30° C. The suspension is stirred at ambient temperature for 3 h. The mixture is treated with water and then it is extracted with ethyl acetate. The title compound is isolated by flash chromatography. By this method 7.0 g of a colorless solid are obtained.

Workup

  1. additionDuring the addition there
  2. stirringThe suspension is stirred at ambient temperature for 3 h
  3. extractionit is extracted with ethyl acetate

Sources & evidence

ORD record
ord-fcf8b3a8a3d441d3b874012de1c0044f
Source dataset
uspto-grants-2014_08
Patent number
US08815855B2

Reaction notes

Loading…