Styrene → HCID 15319530, compound

HRID 1068854Notes

Reaction equation

HRID 1068854 reaction equation
Br[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[C:15]1(/[CH:14]=[CH:13]/[C:2]2[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 7501StyreneHCID 8471TriethylamineHCID 80186Ethyl 2-bromobenzoate

Product 1

HCID 15319530HCID 15319530, compoundYield 103.9%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

8.9 g (38.9 mmol) of ethyl 2-bromobenzoate, 5.1 g (49.4 mmol) of styrene, 0.18 g (0.8 mmol) of palladium diacetate, 0.48 g (1.6 mmol) of tri-o-tolylphosphine and 5 g (49.1 mmol) of triethylamine were reacted in 90 ml of anhydrous acetonitrile at 100° C. for 23 h. The mixture was then filtered and the filtrate was diluted with ethyl acetate, washed with water, dried and concentrated under reduced pressure. 10.2 g (100%) of the product were obtained.

Workup

  1. filtrationThe mixture was then filtered
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39ee49f4dcd7426aab2ee6dafa0b3f7a
Source dataset
uspto-grants-2001_06
Patent number
US06251917B1

Reaction notes

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