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

HRID 583620

Reaction equation

HRID 583620 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21584099Diethylether hexaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-261ccc9e8f3f4021a98e0d660008e1ff
Source dataset
uspto-grants-1999_07
Patent number
US05929273

Linked notes

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