Trifluoroacetic acid → (2-Bromophenyl)(2,4,6-trimethoxybenzyl)sulfane

HRID 1158196

Reaktionsgleichung

Reaktionsgleichung von HRID 1158196
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[C:4]=1[CH2:13]O.[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[SH:22].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22][CH2:13][C:4]1[C:5]([O:11][CH3:12])=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=1[O:2][CH3:1]

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 805982-BromobenzenethiolHCID 516892Sodium BicarbonateHCID 6025152,4,6-Trimethoxybenzyl alcohol

Produkt 1

HCID 66870845(2-Bromophenyl)(2,4,6-trimethoxybenzyl)sulfaneAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 30.8 g (2,4,6-trimethoxyphenyl)methanol (155.4 mmol) and 29.2 g 2-bromobenzenethiol (155.4 mmol) in 150 ml DCM at 0° C. was added dropwise 1.3 eq TFA. The reaction was stirred 15 minutes at room temperature before saturated NaHCO3 was added until neutral. The organic volatiles were removed under reduced pressure and the aqueous residue was extracted with ethyl acetate (3×150 ml). The organic layer was collected, washed with brine and dried over magnesium sulfate, filtered, and concentrated under reduced pressure afforded a yellowish solid. The solid was washed with ethyl acetate to yield 51.3 g white solid (2-bromophenyl)(2,4,6-trimethoxybenzyl)sulfane (13.9 mmol, 89% yield).

Aufarbeitung

  1. additionwas added until neutral
  2. customThe organic volatiles were removed under reduced pressure
  3. extractionthe aqueous residue was extracted with ethyl acetate (3×150 ml)
  4. customThe organic layer was collected
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customafforded a yellowish solid
  10. washThe solid was washed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-bd4f2fbbd3eb4c8c890c74f9239d0878
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807713B2

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