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Dimethyl Sulfoxide → 4-Bromo-4'-(trifluoromethoxy)biphenyl-3-carbaldehyde

HRID 1880568
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1880568
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)=[CH:14][C:13]=1[CH2:29][OH:30].C(N(CC)CC)C>C(Cl)Cl>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]([O:24][C:25]([F:27])([F:28])[F:26])=[CH:22][CH:23]=2)=[CH:14][C:13]=1[CH:29]=[O:30]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67485623[4-Bromo-4'-(trifluoromethoxy)biphenyl-3-yl]methanol

Produkt 1

HCID 866212244-Bromo-4'-(trifluoromethoxy)biphenyl-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

DMSO (0.69 mL, 9.72 mmol) was added dropwise to oxalyl chloride (0.42 mL, 4.86 mmol) in 4 mL DCM at −78° C. After 20 minutes a DCM solution (6 mL) of the intermediate from Step C (1.2 g, 3.47 mmol) was added dropwise. After stirring for 15 minutes at −78° C. triethylamine (2.42 mL, 17.35 mmol) was added. The reaction mixture was then allowed to warm to room temperature. The solution was partitioned between aqueous saturated NH4Cl and DCM. The organic phase was washed with water, brine, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. 1H NMR (500 MHz, CDCl3): δ 10.43 (s, 1H); 8.12 (d, J=2.4 Hz, 1H); 7.75 (d, J=8.6 Hz, 1H); 7.67-7.65 (m, 1H); 7.63 (d, J=8.5 Hz, 2H); 7.34 (d, J=8.5 Hz, 2H). LCMS1 4.09 min. (M+H)=345

Aufarbeitung

  1. additionwas added
  2. customThe solution was partitioned between aqueous saturated NH4Cl and DCM
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-abe076a363ca43a8a40e59bf3be8bd92
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08318760B2

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