Water → HCID 10924661, compound

HRID 1068860Notes

Reaction equation

HRID 1068860 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)=[CH2:2].Br[C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(N(CC)CC)C.O>C(#N)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1/[CH:1]=[CH:2]/[C:21]1[CH:22]=[CH:23][CH:24]=[CH:14][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 132302-VinylnaphthaleneHCID 80186Ethyl 2-bromobenzoate

Product 1

HCID 10924661HCID 10924661, compoundYield 86.5%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

29.7 g (0.13 mol) of 2-vinylnaphthalene, 25 g (0.16 mol) of ethyl 2-bromobenzoate, 22.5 ml (0.16 mol) of triethylamine, 0.54 g of palladium diacetate and 1.44 g of triphenylphosphine in 200 ml of acetonitrile were heated to 100° C. for 20 h. The reaction mixture was then poured into water and the mixture was extracted repeatedly with ethyl acetate. The organic phase was concentrated under reduced pressure and the residue was purified chromatographically on silica gel. 34 g (71%) of the product were obtained.

Workup

  1. extractionthe mixture was extracted repeatedly with ethyl acetate
  2. concentrationThe organic phase was concentrated under reduced pressure
  3. customthe residue was purified chromatographically on silica gel

Sources & evidence

ORD record
ord-24931f057c8b48bd9d6020b92db90fbd
Source dataset
uspto-grants-2001_06
Patent number
US06251917B1

Reaction notes

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