N-bromobutanimide → 5-(bromomethyl)-2,2-difluorobenzo[d][1,3]dioxole

HRID 2419348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2419348
[F:1][C:2]1([F:12])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:4]=2[O:3]1.[Br:13]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[F:12][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][Br:13])=[CH:10][C:4]=2[O:3]1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 138788692,2-Difluoro-5-methyl-2H-1,3-benzodioxole

Produkt 1

HCID 203113835-(bromomethyl)-2,2-difluorobenzo[d][1,3]dioxoleAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel2×

Versuchsvorschrift

A mixture of 2,2-difluoro-5-methyl-1,3-benzodioxole (29.0 g, 0.169 mole), N-bromosuccinimide (30.1 g, 0.169 mole), benzoyl peroxide (0.5 g) and carbon tetrachloride (50 ml) is refluxed for 2.5 hours. Carbon tetrachloride (50 ml) is then added to the hot reaction mixture and the solids are filtered off. The filtrate and washings are evaporated to yield 41.0 g of product as a brown oil; nmr (CCl4) δ 4.38 (S, 2H), 6.8-7.4 (m, 3H). The product is used without purification in the next step.

Aufarbeitung

  1. temperatureis refluxed for 2.5 hours
  2. filtrationthe solids are filtered off
  3. customThe filtrate and washings are evaporated

Quellen und Nachweise

ORD-Eintrag
ord-2b91703464e34a3aa3aaa7cb8ee458d3
Quelldatensatz
uspto-grants-1978_08
Patentnummer
US04105780

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