N,N-Dimethylaniline → Methyl 3-bromo-6-(3-chlorobenzenesulphonylmethyl)-2-hydroxybenzoate

HRID 2177727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2177727
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[C:7]([O:27]C)=[C:8]([C:13]([CH2:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)(=[O:19])=[O:18])=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10].CN(C)C1C=CC=CC=1>C(Cl)Cl>[Br:5][C:6]1[C:7]([OH:27])=[C:8]([C:13]([CH2:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)(=[O:19])=[O:18])=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10]

Komponenten

5

Edukt 3

HCID 949N,N-DimethylanilineHCID 6451240Aluminum(III) ChlorideHCID 67107903Methyl 3-bromo-6-(3-chlorobenzenesulphonylmethyl)-2-methoxybenzoate2×

Produkt 1

HCID 67107545Methyl 3-bromo-6-(3-chlorobenzenesulphonylmethyl)-2-hydroxybenzoateAusbeute 82,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Aluminium chloride (0.7 g) was added to a stirred solution of methyl 3-bromo-6-(3-chlorobenzenesulphonylmethyl)-2-methoxybenzoate (Intermediate 68, 0.76 g) and N,N-dimethylaniline (1.27 g) in DCM (8 ml) and the resultant mixture was stirred for 30 minutes. The mixture was partitioned between ethyl acetate and hydrochloric acid (1M) and the organic layer was washed with sodium bicarbonate (saturated aqueous solution), dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was triturated with ether. The solid was collected by filtration to give methyl 3-bromo-6-(3-chlorobenzenesulphonylmethyl)-2-hydroxybenzoate (0.61 g) as a white solid.

Aufarbeitung

  1. customThe mixture was partitioned between ethyl acetate and hydrochloric acid (1M)
  2. washthe organic layer was washed with sodium bicarbonate (saturated aqueous solution)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was triturated with ether
  7. filtrationThe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-1d9cded88b564d32aaa1bfe7c869971c
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067905B2

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