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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 429598Erstellt: 25. Oktober 2026

2,6-Dimethylaniline → HCID 12010733, Verbindung

https://huagongshe.com/reaction/429598

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt2,6-DimethylanilineHCID 6896—
Edukt2-(2-Bromophenyl)-2-methyl-1,3-dioxolaneHCID 615284—
EduktSodium t-butoxideHCID 23676156—
Katalysator(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumHCID 6505921—
LösungsmittelTolueneHCID 1140—
LösungsmittelDiethyl EtherHCID 3283—
ProduktHCID 12010733HCID 12010733—

Reaktionsbedingungen

Temperatur105 °C

Reaktionsschritte

A mixture of 2-(2′-bromophenyl)-2-methyl-1,3-dioxolane (362 mg, 1.49 mmol), 2,6-dimethylaniline(189 mg, 1.56 mmol), NaOtBu (172 mg, 1.79 mmol), Pd(dba)2 (17 mg, 0.03 mmol), ligand A (21 mg, 0.06 mmol) in toluene (4 mL) was heated to 105° C. for 4.5 hours. The reaction was cooled to room temperature, taken up in diethyl ether (125 mL), washed with water (2×30 mL) and brine (30 mL), dried over MgSO4, filtered and concentrated under vacuum. The crude product was purified by column chromatography on silica gel using hexane (or hexanes: ethyl acetate) as the eluent to afford compound 2b-1, after drying under vacuum, as an off-white solid (yield: 391 mg, 93%) 1H NMR (CDCl3): δ7.41 (dd, 1H, J=7.8, 1.8 Hz, ArH), 7.13-6.99 (m, 4H, ArH), 6.70 (dt, 1H, J=7.5, 1.2 Hz, ArH), 6.15 (dd, 1H, J=7.8, 0.9, ArH), 4.12 (m, 2H, O—CH—CH—O), 3.93 (m, 2H, O—CH—CH—O), 2.18 (s, 6H, Ar—CH3), 1.84 (s, 3H, CH3). 13C NMR (CDCl3): δ143.5, 138.6, 135.2, 129.1, 128.5, 126.3, 125.6, 125.2, 117.3, 112.6, 109.8, 64.1, 24.1, 18.3. Anal. for C18H21NO2; Calcd: C, 76.29, H, 7.47; N, 4.94; Found: C, 75.86; H, 7.46; N, 4.89.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS06316663B1
Quelldatensatzuspto-grants-2001_11
ORD IDord-1f24f6e5335f45748a36c3ff94e91552
Quellennotizuspto-grants-2001_11