Triphenylphosphine → HCID 22009002, compound

HRID 322026Notes

Reaction equation

HRID 322026 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:3]=1.[CH2:15]([Sn](CCCC)(CCCC)CCCC)[CH:16]=[CH2:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Li+].[Cl-]>CN(C=O)C.CCOCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:17]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:3]=1)[CH:16]=[CH2:15]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 90628AllyltributylstannaneHCID 961653-Bromodiphenyl etherHCID 433294Lithium Chloride

Product 1

HCID 22009002HCID 22009002, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 1-bromo-3-phenoxybenzene (2.01 g; 8.08 mmol), PdCl2(PPh3)2 (296 mg; 0.42 mmol), allyl tributyltin 3.13 g; 9.46 mmol), triphenylphosphine (455 mg; 1.73 mmol) and LiCl (1.39 g; 33 mmol) in 10 ml DMF was stirred at 100° C. for 3 h. After cooling to r.t the mixture was diluted with Et2O (75 ml), washed with water (3×50 ml) and brine, dried over MgSO4 and concentrated. Flash chromatography with hexane afforded the desired material.

Workup

  1. temperatureAfter cooling
  2. washwashed with water (3×50 ml) and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4bfbaf8f9e034294bf609b6228685311
Source dataset
uspto-grants-2001_04
Patent number
US06211197B1

Reaction notes

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