Potassium Carbonate → Methyl 2-(4-acetyl-2-(3-trifluoromethylphenyl)phenoxy)acetate

HRID 68598

Reaktionsgleichung

Reaktionsgleichung von HRID 68598
[C:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:6](Br)[CH:5]=1)(=[O:3])[CH3:2].[F:17][C:18]([F:29])([F:28])[C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CC(O)(C)C.O.CCOC(C)=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:6]([C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([C:18]([F:29])([F:28])[F:17])[CH:24]=2)[CH:5]=1)(=[O:3])[CH3:2]

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 66868355Methyl 2-(4-acetyl-2-bromophenoxy)acetate

Produkt 1

HCID 66868647Methyl 2-(4-acetyl-2-(3-trifluoromethylphenyl)phenoxy)acetateAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl 2-(4-acetyl-2-bromophenoxy)acetate (16) (710 mg, 2.5 mmol, 1 eq), 3-(trifluoromethyl)phenylboronic acid (709 mg, 3.75 mmol, 1.5 eq, Aldrich, Milwaukee, Wis., USA) and tetrakis(triphenylphosphine) palladium (100 mg, 0.086 mmol, 0.03 eq) were dissolved in t-BuOH (1 mL) and K2CO3 (1 mL of a 4 M solution in H2O) and heated in a microwave at 120° C. for 20 min. The resultant reaction mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The obtained residue was purified via silica gel chromatography (20% EtOAc/hexane) to give 650 mg (74%) of methyl 2-(4-acetyl-2-(3-trifluoromethylphenyl)phenoxy)acetate (17) as white solid. 1HNMR (CDCl3, 400 MHz): δ 8.43 (s, 2H), 7.90 (m, 2H), 7.60 (m, 2H), 6.89 (d, 1H), 4.72 (s, 2H), 3.79 (s, 3H), 2.59 (s, 3H). MS (ES-API): M+1=353.1. HPLC (Method B) tR=3.28 min.

Aufarbeitung

  1. customThe resultant reaction mixture
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified via silica gel chromatography (20% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-16b8d4de58c946429df3be172cccdbe0
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822467B2

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