N-bromobutanimide → 2-Bromo-1-(quinolin-8-yl)ethan-1-one

HRID 1055940Notes

Reaction equation

[Si]([O:8][C:9]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1[N:19]=[CH:18][CH:17]=[CH:16]2)=[CH2:10])(C(C)(C)C)(C)C.C1C(=O)N([Br:28])C(=O)C1>C1COCC1.O>[Br:28][CH2:8][C:9]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1[N:19]=[CH:18][CH:17]=[CH:16]2)=[O:10]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 8-(1-((tert-butyldimethylsilyl)oxy)vinyl)quinoline (300 mg, 1.045 mmol) in THF (5 mL) and water (1 mL) was added NBS (203 mg, 1.149 mmol), and the resulting mixture was stirred at 25° C. for 30 min. The mixture was diluted with water (5 mL) and extracted in to EtOAc (2×5 mL). The combined extracts were dried over Na2SO4, filtered, and concentrated in vacuo to yield crude 2-bromo-1-(quinolin-8-yl)ethanone (200 mg) (used without further purification in subsequent transformations): 1H NMR (400 MHz, DMSO-d6) δ 8.99-8.98 (1H, m), 8.27-8.23 (1H, m), 8.17-8.15 (1H, m), 7.67-7.63 (1H, m), 5.18 (1H, s), 5.02 (1H, s), 2.78 (2H, s). m/z (ESI, +ve) 249.9 (M+H)+.

Workup

extractionextracted in to EtOAc (2×5 mL)
dry with materialThe combined extracts were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1fe05467f2994b4f80b07705dcbdeb3a
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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