Phenylboronic Acid → (2-Phenyl-3,4,5-trimethoxyphenyl)diphenylphosphine oxide

HRID 481115Notes

Reaction equation

HRID 481115 reaction equation
I[C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[P:14](=[O:27])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:28]1([C:2]2[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[C:5]([O:12][CH3:13])=[CH:4][C:3]=2[P:14](=[O:27])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 66827Phenylboronic AcidHCID 14906789(2-Iodo-3,4,5-trimethoxyphenyl)diphenylphosphine oxide

Product 1

HCID 12996245(2-Phenyl-3,4,5-trimethoxyphenyl)diphenylphosphine oxideYield 98%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a 2 liter Schlenk flask was added (2-iodo-3,4,5-trimethoxyphenyl) diphenylphosphine oxide 21 (30 g, 61 mmol), phenylboronic acid (11.1 g, 91 mmol), and degassed THF (800 ml). A solution of degassed saturated K2CO3 (400 ml) was added afterwards. The whole mixture was degassed with nitrogen for an additional 10 min. Then, Pd(PPh3)4 (1.22 mmol, 1.4 g) was added in the solution through one portion. The mixture was stirred at reflux under nitrogen for 24 hrs. In situ 31PNMR showed that the reaction was complete. The reaction mixture was concentrated under reduced pressure to remove THF and 400 ml of CH2Cl2 was then added. The CH2Cl2 layer was washed with water (200 ml) and brine (200 ml), dried over Na2SO4, and evaporated. The solid residue was recrystallized from EtOAc (100 ml) to give off-white product 22 (23 g). The mother liquid was passed through a silica gel column to give another 4 g of product 22. The total yield was 98%.

Workup

  1. customdegassed THF (800 ml)
  2. additionA solution of degassed saturated K2CO3 (400 ml) was added afterwards
  3. customThe whole mixture was degassed with nitrogen for an additional 10 min
  4. temperatureat reflux under nitrogen for 24 hrs
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customto remove THF and 400 ml of CH2Cl2
  7. additionwas then added
  8. washThe CH2Cl2 layer was washed with water (200 ml) and brine (200 ml)
  9. dry with materialdried over Na2SO4
  10. customevaporated
  11. customThe solid residue was recrystallized from EtOAc (100 ml)

Sources & evidence

ORD record
ord-136e6b29963745baa27c925c0d687b51
Source dataset
uspto-grants-2003_11
Patent number
US06653485B2

Reaction notes

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