1,3-Dibromobenzene → 3-Bromo-N,N-diphenylaniline

HRID 716593ノート

反応式

HRID 716593 の反応式
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[N:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 3

HCID 79271,3-DibromobenzeneHCID 11487DiphenylamineHCID 23676156Sodium t-butoxide

生成物 1

HCID 162178513-Bromo-N,N-diphenylaniline収率 78.1%

試薬・触媒・溶媒 3

HCID 11776Triphenylphosphine触媒HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

実験手順

Diphenylamine (9 g, 53.3 mmol), and 1,3-dibromobenzene (25 g, 106.8 mmol) were mixed in toluene (500 mL). The solution was bubbled nitrogen while stirring for 15 min. Pd(OAc)2 (0.18 g, 0.8 mmol), triphenylphosphine (0.84 g, 3.2 mmol) and tBuONa (7.7 g, 80.2 mmol) were added in sequence. The mixture was heated to reflux overnight under nitrogen. After cooling, the reaction mixture was filtered through Celite®/silica pad and the solvent was then evaporated. The residue was purified by column using hexane as eluent to obtain 13.5 g (60%) of 3-bromo-N,N-diphenylaniline.

後処理

  1. customThe solution was bubbled nitrogen
  2. temperatureThe mixture was heated
  3. temperatureto reflux overnight under nitrogen
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture was filtered through Celite®/silica pad
  6. customthe solvent was then evaporated
  7. customThe residue was purified by column

出典と根拠

ORDレコード
ord-708c4296c60045d7afdf6423e8e4a2a8
出典データセット
uspto-grants-2015_11
特許番号
US09190623B2

反応ノート

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