1,2-Dichloroethane → N-(3-phenoxyphenyl)[(3-bromophenyl)methyl]amine

HRID 990419

Reaktionsgleichung

Reaktionsgleichung von HRID 990419
ClCCCl.[Br:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=O.[O:14]([C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>O.C(O)(=O)C>[O:14]([C:21]1[CH:22]=[C:23]([NH:24][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[C:6]([Br:5])[CH:7]=2)[CH:25]=[CH:26][CH:27]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 765833-BromobenzaldehydeHCID 771353-PhenoxyanilineHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 11046431N-(3-phenoxyphenyl)[(3-bromophenyl)methyl]amineAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

EX-595A) To a 1,2-dichloroethane (90 mL) solution of 3-bromobenzaldehyde (5.60 g, 30.3 mmol) was added 3-phenoxyaniline (5.60 g, 30.2 mmol), NaB(OAc)3H (8.26 g, 39.0 mmol) and acetic acid (1.8 mL, 31. mmol). The cloudy solution was stirred at room temperature for 1.5 h. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with saturated NaHCO3 and brine, dried (MgSO4) and evaporated to yield 10.49 g (98%) of the desired N-(3-phenoxyphenyl)[(3-bromophenyl)methyl]amine product as a light brown oil. 1H NMR (CDCl3) δ4.26 (s, 2H), 6.27 (s, 1H), 6.38 (d, 2H), 7.00 (d, 2H), 7.13 (m, 2H), 7.19 (t, 1H), 7.26 (d, 1H), 7.30 (m, 2H), 7.38 (d, 1H), 7.96 (s, 1H). The formation of the desired product was monitored by the disappearance of the aldehyde peak (δ˜10) and the formation of the benzyl peak (6 4.26) in the 1H NMR spectrum.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with saturated NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-36694002a0fe46af96afdd51bdd00791
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458803B1

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