Carbon tetrabromide → HCID 67395877, Verbindung

HRID 714646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714646
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[C:13]([CH2:15]O)[CH:12]=[CH:11][N:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:39]>C1COCC1>[Br:39][CH2:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:18])([F:17])[F:1])[CH:14]=1

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67056312HCID 67056312, Verbindung

Produkt 1

HCID 67395877HCID 67395877, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

495 mg (1.96 mmol) of the compound from Example 61A and 615 mg (2.35 mmol) of triphenylphosphine were dissolved in 15 ml of THF, and 778 mg (2.35 mmol) of carbon tetrabromide were added at RT. After the addition had ended, the mixture was stirred ar RT for 16 h. For work-up, the mixture was filtered through 20 g of kieselguhr and the filtrate was concentrated under reduced pressure. The residue was purified chromatographically on silica gel (mobile phase: first cyclohexane/ethyl acetate 70:30, then ethyl acetate). This gave, in a purity of 90%, 149 mg (22% of theory) of the target compound, which were immediately reacted further.

Aufarbeitung

  1. additionAfter the addition
  2. filtrationFor work-up, the mixture was filtered through 20 g of kieselguhr
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified chromatographically on silica gel (mobile phase
  5. customThis gave, in a purity of 90%, 149 mg (22% of theory) of the target compound, which were immediately reacted further

Quellen und Nachweise

ORD-Eintrag
ord-c349bd00839048d98bbe3cf67501adf6
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187466B2

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