Trifluoroacetic acid → 1-Benzyl-4-bromo-2,5-dimethoxybenzene

HRID 1486832

Reaktionsgleichung

Reaktionsgleichung von HRID 1486832
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][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.[NH4+].[Cl-]>C(Cl)Cl.O>[CH2:10]([C:5]1[CH:6]=[C:7]([O:8][CH3:9])[C:2]([Br:1])=[CH:3][C:4]=1[O:18][CH3:19])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 25517Ammonium ChlorideHCID 67466544(4-Bromo-2,5-dimethoxyphenyl)(phenyl)methanone

Produkt 1

HCID 900142701-Benzyl-4-bromo-2,5-dimethoxybenzeneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of (4-bromo-2,5-dimethoxyphenyl)(phenyl)methanone (100 mg, 0.311 mmol) in 0.2 mL of anhydrous DCM (C=1.5M), were successively added dropwise trifluoroacetic acid (0.24 mL, 10 eq) and triethylsilane (0.2 mL, 4 eq). After 16 h of stirring at r.t., the reaction mixture was hydrolyzed with a saturated NH4Cl solution (5 mL). The layers were diluted with 20 mL of DCM and 20 mL of water and then separated. The aqueous layer was extracted twice with DCM (2×10 mL) The combined organic phase was washed twice with a saturated NaHCO3 solution (2×20 mL), brine (2×20 mL), dried over MgSO4, filtered and concentrated in vacuo. The product was obtained pure enough for further reaction in 98% yield (93.4 mg). 1H NMR (300 MHz, CDCl3) δ 7.34-7.25 (m, 2H), 7.24-7.17 (m, 3H), 7.08 (s, 1H), 6.69 (s, 1H), 3.95 (s, 2H), 3.78 (s, 3H), 3.78 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 151.9 (C), 150.1 (C), 140.4 (C), 129.9 (C), 128.9 (CH), 128.5 (CH), 126.1 (CH), 116.1 (CH), 115.0 (CH), 109.1 (C), 57.0 (OCH3), 56.3 (OCH3), 35.9 (CH2Bn); MS (ESI) m/z: 324.5, 326.1 [M+NH4, 79Br, 81Br]+; 630.3, 632.0, 634.2 [2M+NH4, 79Br, 81Br]+.

Aufarbeitung

  1. customseparated
  2. extractionThe aqueous layer was extracted twice with DCM (2×10 mL) The combined organic phase
  3. washwas washed twice with a saturated NaHCO3 solution (2×20 mL), brine (2×20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was obtained pure enough for further reaction in 98% yield (93.4 mg)

Quellen und Nachweise

ORD-Eintrag
ord-88ac974de66b4622ad2bda627e7d8eaf
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428500B2

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