N-bromobutanimide → 1-tert-Butyloxycarbonyl-2-bromo-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyrrole

HRID 1906496Notes

Reaction equation

HRID 1906496 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[C:9]1[C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:30]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[C:9]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:27])=[O:28])=[CH:22][CH:21]=2)=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:11]=[C:12]1[Br:30])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 100932901-tert-Butyloxycarbonyl-2-(4-methylsulfonylphenyl)-3-(4-fluorophenyl)pyrrole

Product 1

HCID 100972521-tert-Butyloxycarbonyl-2-bromo-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyrrole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 1-tert-butyloxycarbonyl-2-(4-methylsulfonylphenyl)-3-(4-fluorophenyl)pyrrole (13.5 g, 0.032 mole) in 100 ml N,N'-dimethylformamide was treated with a solution of N-bromosuccinimide (5.7 g, 0.032 mole) in 50 ml N,N'-dimethylformamide. The mixture was stirred for four hours at room temperature and poured into a mixture of 500 ml 5% sodium bicarbonate and 500 g of ice. The resulting solid was collected by filtration, washed with water, and dried. The crude product was recrystallized from diethyl ether/hexanes to yield 11.0 g (68%); m.p. 121° dec.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with water
  3. customdried
  4. customThe crude product was recrystallized from diethyl ether/hexanes
  5. customto yield 11.0 g (68%)

Sources & evidence

ORD record
ord-fb2790b6f0564563b43acf37068fcb08
Source dataset
uspto-grants-1987_03
Patent number
US04652582

Reaction notes

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