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

HRID 48047

반응식

HRID 48047 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 11046431N-(3-phenoxyphenyl)[(3-bromophenyl)methyl]amine수율 98.1%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

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 (δ 4.26) in the H NMR spectrum.

후처리

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

출처 및 근거

ORD 기록
ord-f431acb3b4cb4da0952e1ed92a25bb38
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699898B2

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