6-Bromo-2,2,4,4-tetrafluoro-1,3-benzodioxane → 2,2,4,4-tetrafluoro-4H-benzo[1,3]dioxine-6-carboxylic acid methyl ester

HRID 401548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401548
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([F:12])([F:11])[O:8][C:7]([F:14])([F:13])[C:6]=2[CH:15]=1>CO.CC#N.CCN(CC)CC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:7][O:8][C:9]([C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([F:12])([F:11])[O:8][C:7]([F:14])([F:13])[C:6]=2[CH:15]=1)=[O:10]

Komponenten

6

Edukt 1

HCID 27734106-Bromo-2,2,4,4-tetrafluoro-1,3-benzodioxane

Produkt 1

HCID 591661662,2,4,4-tetrafluoro-4H-benzo[1,3]dioxine-6-carboxylic acid methyl esterAusbeute 169,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A suspension of 6-bromo-2,2,4,4-tetrafluoro-4H-benzo[1,3]dioxine (4.75 g, 16.6 mmol) and Pd(PPh3)4 (950 mg, 8.23 mmol) in MeOH (20 mL), MeCN (30 mL) and Et3N (10 mL) was stirred under carbon monoxide atmosphere (55 psi) at 75° C. (oil bath temperature) overnight. The cooled reaction mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel column (Petroleum Ether) to give 2,2,4,4-tetrafluoro-4H-benzo[1,3]dioxine-6-carboxylic acid methyl ester (3.75 g, 85%). 1H NMR (CDCl3, 300 MHz) δ 8.34 (s, 1H), 8.26 (dd, J=2.1, 8.7 Hz, 1H), 7.22 (d, J=8.7 Hz, 1H), 3.96 (s, 3H).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel column (Petroleum Ether)

Quellen und Nachweise

ORD-Eintrag
ord-927c15d7aaf2425bba98150dc6294594
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741933B2

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