N-bromobutanimide → 2-(Bromomethyl)-6-methoxynaphthalene

HRID 974665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 974665
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 110193292-METHOXY-6-METHYLNAPHTHALENE

Produkt 1

HCID 100377832-(Bromomethyl)-6-methoxynaphthaleneAusbeute 69,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel2×

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

A solution of 2-methyl-6-methoxynaphthalene (4.lg, 23.8 mmole) and azoisobutyronitrile (80 mg) in dry carbon tetrachloride (30 ml) was heated to reflux with stirring. A slurry of N-bromosuccinimide (4.6 g, 25.8 mmole) and azoisobutyronitrile (20 mg) in dry carbon tetrachloride (10 ml) was added gradually over 2 hours. The resulting solution was heated under reflux for 30 minutes and then cooled to 35° C. The succinimide was filtered off and washed with carbon tetrachloride (5 ml). The filtrate was evaporated to dryness to afford a creamy coloured solid which was dried under vacuum at 40° C. It weighed 5.8 g and contained 70.3% 2-bromomethyl-6-methoxynaphthalene giving an activity yield of 69.5%.

Aufarbeitung

  1. temperatureto reflux
  2. temperatureThe resulting solution was heated
  3. temperatureunder reflux for 30 minutes
  4. filtrationThe succinimide was filtered off
  5. washwashed with carbon tetrachloride (5 ml)
  6. customThe filtrate was evaporated to dryness
  7. customto afford a creamy coloured solid which
  8. customwas dried under vacuum at 40° C

Quellen und Nachweise

ORD-Eintrag
ord-2bcc8b676a6440c7b7f39d7c278d762e
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05068458

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