Dichloromethane → Methyl 2-(bromomethyl)-6-chlorobenzoate

HRID 630256

Reaktionsgleichung

Reaktionsgleichung von HRID 630256
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.ClCCl>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:2]([Cl:1])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 22935202Methyl 2-chloro-6-methylbenzoate

Produkt 1

HCID 22935208Methyl 2-(bromomethyl)-6-chlorobenzoateAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-chloro-6-methylbenzoate (3.0 g, 16.2 mmol), N-bromosuccinimide (3.0 g, 17.0 mmol), and benzoyl peroxide (catalytic) in anhydrous carbon tetrachloride (50 mL) was stirred at reflux overnight. Dichloromethane (50 mL) was added after cooling to room temperature. The mixture was extracted with 1 N NaOH (2×100 mL). The organic layer was recovered, dried over MgSO4, filtered, and evaporated, and the residue was dried in vacuo, affording methyl 2-(bromomethyl)-6-chlorobenzoate (4.06 g, 95% yield), which was used without further purification.

Aufarbeitung

  1. temperatureat reflux overnight
  2. extractionThe mixture was extracted with 1 N NaOH (2×100 mL)
  3. customThe organic layer was recovered
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-334dbdca68bc46a7a4f87c4f2025cff3
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315521B2

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