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 1008818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1008818
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, 1 H), 8.26 (dd, J=2.1, 8.7 Hz, 1 H), 7.22 (d, J=8.7 Hz, 1 H), 3.96 (s, 3 H).

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-657d50df88f04af79f219ec75005185c
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973038B2

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