Triethylsilane → 6-(2-Bromo-5-iodobenzyl)-2,3-dihydrobenzo[b][1,4]dioxine

HRID 1914496

Reaktionsgleichung

Reaktionsgleichung von HRID 1914496
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:20]=[CH:19][C:14]2[O:15][CH2:16][CH2:17][O:18][C:13]=2[CH:12]=1)=O.C([SiH](CC)CC)C.OS(C(F)(F)F)(=O)=O>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[CH2:9][C:11]1[CH:20]=[CH:19][C:14]2[O:15][CH2:16][CH2:17][O:18][C:13]=2[CH:12]=1

Komponenten

5

Edukt 3

HCID 12052TriethylsilaneHCID 62406Trifluoromethanesulfonic acidHCID 58340798Methanone, (2-bromo-5-iodophenyl)(2,3-dihydro-1,4-benzodioxin-6-yl)-

Produkt 1

HCID 583408306-(2-Bromo-5-iodobenzyl)-2,3-dihydrobenzo[b][1,4]dioxineAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

To a stirred solution of (2-bromo-5-iodo-phenyl)-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanone (30.0 g, 67.4 mmol) in trifluoroacetic acid (100 mL) was added triethylsilane (86.2 mL, 539.3 mmol) followed by triflic acid (6.0 mL, 67.42 mmol) at room temperature. After stirring for 25 min at room temperature, volatiles were evaporated under reduced pressure. The resulting residue was taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution (200 mL×2), water (200 mL), and brine (200 mL), then dried over sodium sulfate, concentrated and purified by silica gel column chromatography to furnish 6-(2-bromo-5-iodo-benzyl)-2,3-dihydro-benzo[1,4]dioxine (26.5 g).

Aufarbeitung

  1. customvolatiles were evaporated under reduced pressure
  2. washwashed with saturated aqueous sodium bicarbonate solution (200 mL×2), water (200 mL), and brine (200 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4705230df03e4b67bca35f5a3e5c2779
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614195B2

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