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

HRID 1017065

反応式

HRID 1017065 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

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 (δ4.26) in the 1H NMR spectrum.

後処理

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

出典と根拠

ORDレコード
ord-c2340af412e14c50b333bf3b2ee63ed9
出典データセット
uspto-grants-2002_11
特許番号
US06476075B1

関連ノート

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