2,2'-Bis(bromomethyl)-1,1'-biphenyl → 2,2'-Bis{di[p-(3-phenylpropyl)phenyl]phosphinomethyl}-1,1-biphenyl

HRID 583620

反応式

HRID 583620 の反応式
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([P:16]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:20][CH:19]=3)Cl)=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[CH2:47]Br>C1COCC1.CCOCC.CCCCCC>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([P:16]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[CH2:47][P:16]([C:18]3[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH2:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[CH:22][CH:23]=3)[C:13]3[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:11][CH:12]=3)[C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:20][CH:19]=3)=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 2

HCID 2519622,2'-Bis(bromomethyl)-1,1'-biphenylHCID 11113246Di[p-(3-phenylpropyl)phenyl]chlorophosphine

生成物 1

HCID 161512272,2'-Bis{di[p-(3-phenylpropyl)phenyl]phosphinomethyl}-1,1-biphenyl収率 69%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 21584099Diethylether hexane溶媒

実験手順

Di[p-(3-phenylpropyl)phenyl]chlorophosphine 1 (6.0 g, 13.1 mmol) was dissolved in 150 ml THF and Li (0.185 g, 26.2 mmol) was chopped directly into the reaction flask under Ar. A deep red solution was resulted in 10 min and all the lithium was consumed in 4 h. The solution was then filtered and 2,2'-dibromomethyl-1,1'-biphenyl (2.23 g, 6.5 mmol) in 20 ml THF was added dropwise with an ice-water bath. The color of the solution was slowly changed to pale yellow. The mixture was stirred for additional 10 h before the solvent was removed by vacuum. 50 ml diethyl ether was added and it was washed with 3×10 ml H2O. The ether phase was dried over MgSO4 and the solvent was then removed by vacuum. The resulting pale yellow viscous oil was purified over silica gel column. 2.3 g (69% yield) of 11 was eluted with Et2O/hexane (1/10), 11 was characterized by 1H, 13C, 31P NMR and Mass spectrometry.

後処理

  1. customA deep red solution was resulted in 10 min
  2. customall the lithium was consumed in 4 h
  3. filtrationThe solution was then filtered
  4. customwas removed by vacuum
  5. addition50 ml diethyl ether was added
  6. washit was washed with 3×10 ml H2O
  7. dry with materialThe ether phase was dried over MgSO4
  8. customthe solvent was then removed by vacuum
  9. customThe resulting pale yellow viscous oil was purified over silica gel column

出典と根拠

ORDレコード
ord-261ccc9e8f3f4021a98e0d660008e1ff
出典データセット
uspto-grants-1999_07
特許番号
US05929273

関連ノート

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