Bromine → HCID 15729278, compound

HRID 1494416Notes

Reaction equation

HRID 1494416 reaction equation
[CH3:1][C:2]1[N:3]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:4]=[C:5]([C:7](=[O:9])[CH3:8])[CH:6]=1.[Br:19]Br>C(Cl)(Cl)Cl>[CH3:1][C:2]1[N:3]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:11])=[O:12])[CH:4]=[C:5]([C:7](=[O:9])[CH2:8][Br:19])[CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 15729276HCID 15729276, compound

Product 1

HCID 15729278HCID 15729278, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 13.3 g (50 mmole) of 1-(2-methyl-1-phenylsulfonyl-pyrrol-4-yl)-1-ethanone in 320 ml of chloroform was stirred at -10° C. and a solution of 2.56 ml (8.0 g, 50 mmole) of bromine in 40 ml of chloroform was added dropwise over six hours. After the addition was completed, the mixture was stirred at -10° C. for 0.5 hours, then allowed to warm to room temperature. The mixture was concentrated, and the residue was chromatographed over silica gel using 1:1:0.1 hexane/toluene/ethyl acetate as eluent to give 10.0 g (59%) of the product as a white solid; m.p. 86°-88° C.

Workup

  1. additionAfter the addition
  2. temperatureto warm to room temperature
  3. concentrationThe mixture was concentrated
  4. customthe residue was chromatographed over silica gel using 1:1:0.1 hexane/toluene/ethyl acetate as eluent

Sources & evidence

ORD record
ord-a5fb927b658f408d8e9e0c0e387086e4
Source dataset
uspto-grants-1991_06
Patent number
US05026715

Reaction notes

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