Ethylene → HCID 22345111, compound

HRID 432066Notes

Reaction equation

HRID 432066 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]1[C:21]3[C:16](=[CH:17][C:18](Br)=[CH:19][CH:20]=3)[CH:15]=[CH:14][C:13]=1[OH:23])=[C:7]([OH:24])[CH:6]=[CH:5]2.[CH3:25][C:26]1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH3:47][CH2:48]N(CC)CC.C=C>CN(C=O)C.C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:25]([C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][CH:19]=1)[C:12]([C:8]1[C:9]3[C:4](=[CH:3][C:2]([CH:47]=[CH2:48])=[CH:11][CH:10]=3)[CH:5]=[CH:6][C:7]=1[OH:24])=[C:13]([OH:23])[CH:14]=[CH:15]2)=[CH2:26]

Participants

8

Reactant 4

HCID 6325EthyleneHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 2228426,6′-Dibromo[1,1′-binaphthalene]-2,2′-diol

Product 1

HCID 22345111HCID 22345111, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6,6′-dibromo-2,2′-dihydroxy-1,1′-binaphthyl (0.694 g, 1.56 mmol), Pd(OAc)2 (0.020 g, 5 mol %), P(o-tolyl)3 (0.080 g, 15 mol %) and Et3N (0.5 mL) in DMF (2 mL) was pressurized with ethylene (200 psi) at 75° C. for 18 hrs. The resulting mixture was diluted in ethyl acetate (20 mL) and filtered through celite, followed by water (20 mL) and brine (20 mL) washes. The solution was dried over MgSO4 and evaporated to produce a tan solid, which was purified by column chromatography to yield the desired product in 54% yield (0.286 g).

Workup

  1. filtrationfiltered through celite
  2. dry with materialThe solution was dried over MgSO4
  3. customevaporated
  4. customto produce a tan solid, which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-7b932ae919e2453e98a2b3b326d7c830
Source dataset
uspto-grants-2003_12
Patent number
US06660876B2

Reaction notes

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