Trifluoroacetic acid → HCID 90013956, compound

HRID 1486838Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)=[C:4]([O:18][CH3:19])[CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[CH2:10]([C:5]1[C:4]([O:18][CH3:19])=[CH:3][C:2]([Br:1])=[CH:7][C:6]=1[O:8][CH3:9])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

(4-bromo-2,6-dimethoxyphenyl)(phenyl)methanone (87 mg, 0.271 mmol) was solubilized and stirred into a mixture of trifluoroacetic acid (250 μL, 12 eq) and triethylsilane (260 μL, 6 eq) heated at 80° C. for 15 h. After cooling to r.t., 20 mL of DCM were added to the reaction mixture. The organic layer was washed with a saturated NaHCO3 solution (2×20 mL), with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel flash chromatography (cyclohexane/AcOEt 95:5) to afford the reduced compound in 98% yield (81.4 mg) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.28-7.21 (m, 4H), 7.20-7.12 (m, 1H), 6.73 (s, 2H), 3.98 (s, 2H), 3.81 (s, 6H); 13C NMR (75 MHz, CDCl3) δ 158.77 (2C), 141.23 (C), 128.57 (2CH), 128.14 (2CH), 125.63 (CH), 120.45 (C), 116.86 (C), 107.71 (2CH), 56.04 (2OCH3), 28.58 (CH2); MS (ESI) m/z: 307.4, 309.0 [M+H, 79Br, 81Br]+; 324.1, 326.1 [M+NH4, 79Br, 81Br]+.

Workup

temperatureAfter cooling to r.t.
washThe organic layer was washed with a saturated NaHCO3 solution (2×20 mL), with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude residue was purified by silica gel flash chromatography (cyclohexane/AcOEt 95:5)
customto afford the reduced compound in 98% yield (81.4 mg) as a white solid

Sources & evidence

ORD record: ord-2e263f557751405d8bae865741665639
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428500B2

Reaction notes

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