Hydrochloric Acid → HCID 90413539, compound

HRID 1746063Notes

Reaction equation

[F:1][C:2]1([F:15])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([Si:11]([CH3:14])([CH3:13])[CH3:12])[C:4]=2[O:3]1.[Li]C(CC)C.C(O[B:25]1[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]1)(C)C.[NH4+].[Cl-].Cl>O1CCCC1.O>[F:15][C:2]1([F:1])[O:6][C:5]2[C:7]([B:25]3[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]3)=[CH:8][CH:9]=[C:10]([Si:11]([CH3:12])([CH3:14])[CH3:13])[C:4]=2[O:3]1

Participants

Conditions

Temperature: -75 °C

Procedure

(2,2-Difluorobenzo[d][1,3]dioxol-4-yl)trimethylsilane (5.0 g, 22 mmol, prepared as described in Gorecka, Joanna; Leroux, Frederic; Schlosser, Manfred, European Journal of Organic Chemistry 2004, 1, 64-68) was added to a stirred solution of sec-BuLi (1.4 M; 10 mL, 14 mmol) in dry tetrahydrofuran (28 mL) cooled to −75° C. After 2 h at −75° C., 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.2 g, 23 mmol) was added, and the mixture was stirred for 90 min at −75° C. The mixture was treated with saturated NH4Cl (5 mL) and warmed to 20° C. The mixture was combined with water (75 mL), acidified with 6 M HCl and extracted with diethyl ether (100 mL). The organic phase was washed with saturated NaCl (15 mL), dried (Na2SO4) and evaporated to give the title compound (estimated purity of 60%) which was used without further purification: 1H NMR (400 MHz, CDCl3) δ 7.39 (d, J=7.5 Hz, 1H), 7.07 (d, J=7.5 Hz, 1H), 1.36 (s, 12H), 0.33 (s, 9H); 19F NMR (376 MHz, CDCl3) δ −49.33; EIMS m/z 356.

Workup

temperaturewarmed to 20° C
extractionextracted with diethyl ether (100 mL)
washThe organic phase was washed with saturated NaCl (15 mL)
dry with materialdried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-36f29c1814a24549aeb5191ca88703b9
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09149038B2

Reaction notes

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