Butyl bromide → 5-Bromo-1-butyl-1H-indole

HRID 2221252Notes

Reaction equation

[Br:1][CH2:2][CH2:3][CH2:4][CH3:5].Br[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2>>[Br:1][C:2]1[CH:8]=[C:9]2[C:5](=[CH:4][CH:3]=1)[N:12]([CH2:13][CH2:14][CH2:15][CH3:7])[CH:11]=[CH:10]2

Participants

Reactant 2

HCID 8002Butyl bromide

HCID 249055-Bromoindole

Product 1

HCID 131691555-Bromo-1-butyl-1H-indole

Procedure

The title compound was prepared from 1-bromobutane (11 mL, 101 mmol) and 5-bromoindole (20 g, 101 mmol) in substantially the same manner, as described in Step 1 of Example 25. The product was obtained as an oil. Mass spectrum (ESI, [M+H]+) m/z 252. 1HNMR (300 MHz, DMSO-d6): δ 7.71 (d, 1H, J=1.9 Hz), 7.46 (d, 1H, J=8.7 Hz), 7.42 (d, 1H, J=3.1 Hz), 7.22 (dd, 1H, J=6.7 Hz and J=2.0 Hz), 6.40 (d, 1H, J=3.1 Hz), 4.15 (t, 2H, J=7.0 Hz), 1.70 (q, 2H, J=7.0 Hz), 1.19 (h, 2H, J=7.47 Hz), and 0.85 ppm (t, 3H, J=7.47 Hz).

Workup

customThe product was obtained as an oil

Sources & evidence

ORD record: ord-e9086bb703ff4baa9a509f27aaa675b3
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368471B2

Reaction notes

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