Benzenesulfonyl chloride → 4-Bromo-1-(phenylsulfonyl)-1H-indole

HRID 2112456Notes

Reaction equation

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

Participants

Reactant 2

HCID 7369Benzenesulfonyl chloride

HCID 6764944-Bromoindole

Product 1

HCID 220153114-Bromo-1-(phenylsulfonyl)-1H-indole

Procedure

4-Bromo-1-(benzenesulfonyl)-1H-indole was prepared from 4-bromoindole and phenylsulfonyl chloride according to Method 4 to afford 3.1 g (91%) of a light purple solid: 1HNMR (CDCl3) δ 7.94 (d, J=8 Hz, 1H), 7.89-7.84 (m, 2H), 7.62 (d, 4 Hz, 1H), 7.57-7.51 (m, 1H), 7.46-7.37 (m, 3H), 7.19-7.13 (m, 1H), 6.72 (dd, J=1, 4 Hz, 1H); MS (ESI) 419.9+421.9 (M+H)+; Purity (HPLC) >95%.

Sources & evidence

ORD record: ord-7a081a7b880446acab89f551766ab99b
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524839B2

Reaction notes

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