N-bromobutanimide → 3-bromo-1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole

HRID 1585079Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[CH:11][CH:10]=[C:9]2[CH3:23])=[CH:4][CH:3]=1.[Br:24]N1C(=O)CCC1=O>C1COCC1>[Br:24][C:10]1[CH:11]=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]=1[CH3:23]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole (Example 1) (3.3 g, 10 mmol) in THF (80 ml) at -70° C., N-bromosuccinimide (1.78 g, 10 mmol) was added over 10 minutes. The reaction was warmed to 20° C. over 3 hours and stirred for 18 hours. After dilution with aqueous sodium bicarbonate, the mixture was extracted with ethyl acetate. The organic fractions were washed with water, dried (MgSO4), filtered and concentrated. The crude yellowish liquid (4.52 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3) to give 3-bromo-1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole (3.6 g, 88%): mp (DSC) 153° C. Anal Calc'd. for C18H15NSBrFO2 : C, 52.95; H, 3.70; N, 3.43; S, 19.53. Found: C, 53.01; H, 3.93; N, 3.39; S, 19.06.

Workup

extractionAfter dilution with aqueous sodium bicarbonate, the mixture was extracted with ethyl acetate
washThe organic fractions were washed with water
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe crude yellowish liquid (4.52 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3)

Sources & evidence

ORD record: ord-1922136070844a7795f622679da86efe
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05935990

Reaction notes

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