4-Bromobenzaldehyde → 4-(4-Bromo-benzylamino)-2-hydroxy-benzoic acid methyl ester

HRID 18441

Reaktionsgleichung

Reaktionsgleichung von HRID 18441
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[OH:11].[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>CC(O)=O.ClCCCl.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([Br:13])=[CH:15][CH:16]=2)=[CH:6][C:5]=1[OH:11]

Komponenten

8

Edukt 4

HCID 707414-BromobenzaldehydeHCID 77787Methyl p-aminosalicylateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 586858634-(4-Bromo-benzylamino)-2-hydroxy-benzoic acid methyl esterAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 4-amino-2-hydroxy benzoic acid methyl ester (836 mg; 5 mmol) and 4-bromobenzaldehyde (926 mg; 5 mmol) in 1 M HOAc in 1,2-dichloroethane (5 mL) was added at once NaBH(OAc)3 (1.49 g; 7 mmol) and the reaction mixture was stirred at room temperature overnight. Water (25 mL) was added and the inhomogeneous mixture was neutralized using solid NaHCO3. The organic layer was isolated, dried, evaporated to dryness and recrystallised from isopropyl ether/dichloromethane/heptane to yield 970 mg (58%) of a yellow solid. NMR and GC-MS in accordance with structure.

Aufarbeitung

  1. customThe organic layer was isolated
  2. customdried
  3. customevaporated to dryness
  4. customrecrystallised from isopropyl ether/dichloromethane/heptane

Quellen und Nachweise

ORD-Eintrag
ord-27627b1c3a684507b64c67ddba27ff91
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741352B2

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