Benzoyl Peroxide → 3-(Bromomethyl)-2-chlorobenzoic acid

HRID 446369

Reaktionsgleichung

Reaktionsgleichung von HRID 446369
C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Cl:19][C:20]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([OH:24])=[O:23].[Br:30]N1C(=O)CCC1=O>ClC1C=CC=CC=1.C(OCC)(=O)C>[Br:30][CH2:29][C:28]1[C:20]([Cl:19])=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([OH:24])=[O:23]

Komponenten

6

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 1398792-Chloro-3-methylbenzoic acid

Produkt 1

HCID 202214903-(Bromomethyl)-2-chlorobenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7964ChlorobenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Benzoyl peroxide (1.33 g) was added to a suspension of 2-chloro-3-methylbenzoic acid (25 g) and N-bromosuccinimide (28.7 g) in chlorobenzene (250 mL) and the resulting mixture was heated to 85° C. for 4 h. The mixture was diluted with ethyl acetate (100 mL) and washed with 10% aqueous brine (3×100 mL). The organic layer was dried over magnesium sulphate, filtered and evaporated. The beige solid was recrystallised from ethyl acetate (˜75 mL)/isohexane (˜250 mL) to give the subtitled compound as a white solid. Yield 25.3 g.

Aufarbeitung

  1. washwashed with 10% aqueous brine (3×100 mL)
  2. dry with materialThe organic layer was dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe beige solid was recrystallised from ethyl acetate (˜75 mL)/isohexane (˜250 mL)

Quellen und Nachweise

ORD-Eintrag
ord-336c9319b0a741feb0a495d2b211fae1
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476265B2

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