N-bromobutanimide → Methyl 2-(bromomethyl)-5-ethoxybenzoate

HRID 577594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577594
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:14])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])[CH3:2].C1C(=O)N([Br:22])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.[Cl-].[Na+].O>[Br:22][CH2:14][C:7]1[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

Komponenten

6

Edukt 2

HCID 67184N-bromobutanimideHCID 86723821Methyl 5-ethoxy-2-methylbenzoate

Produkt 1

HCID 86723822Methyl 2-(bromomethyl)-5-ethoxybenzoateAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 5943Carbon TetrachlorideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of methyl 5-ethoxy-2-methylbenzoate (134b, 0.700 g, 3.61 mmol) in CCl4 (12 mL) was added BPO (18.0 mg, 0.0720 mmol) and NBS (0.706 g, 3.97 mmol) at room temperature. The resulting mixture was heated at 80° C. for 12 hours under N2 atmosphere. The mixture was diluted with CH2Cl2 (10 mL) and brine (3 mL). The organic layer was separated and washed with NaHCO3 (2 N, 10 mL), H2O (5 mL) and brine (5 mL), dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc=5:1) to give methyl 2-(bromomethyl)-5-ethoxybenzoate (134c, 0.85 g, 86%) as yellow liquid.

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with NaHCO3 (2 N, 10 mL), H2O (5 mL) and brine (5 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography (petroleum ether/EtOAc=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-9039af9cf5a4456791bd97a9e6725b39
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040515B2

Notizen zur Reaktion

Wird geladen…