Sodium Carbonate → (E)-ethyl-3-(4'-chloro-biphenyl-4-yl)-but-2-enoate

HRID 1268261Notes

Reaction equation

HRID 1268261 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH3:15])=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>COCCOC.Cl>[CH2:13]([O:12][C:10](=[O:11])/[CH:9]=[C:8](/[C:5]1[CH:6]=[CH:7][C:2]([C:26]2[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=2)=[CH:3][CH:4]=1)\[CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 15933615(E)-ethyl 3-(4-bromophenyl)-but-2-enoate

Product 1

HCID 22557604(E)-ethyl-3-(4'-chloro-biphenyl-4-yl)-but-2-enoate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Tetrakis(triphenylphoshine)palladium(0) (0.26 g, 0.22 mmol, 4 mol %) was added, under nitrogen, to a stirred solution of (E)-ethyl 3-(4-bromophenyl)-but-2-enoate (1.5 g, 5.57 mmol) {prepared as detailed in example 50 a} in DME (70 ml), and the resulting orange coloured solution stirred at room temperature for 10 min. Aqueous 2M sodium carbonate (16.7 ml, 33.4 mmol) was then added, the mixture stirred for 10 min, then 4-chlorophenyl boronic acid (1.3 g, 8.36 mmol) was added, and the reaction mixture heated to 80° C. for 18 h, under reflux. The reaction mixture was diluted with 1N HCl (100 ml) and the products extracted into ethyl acetate (2×100 ml). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated to give the crude product, which was purified by column chromatography on silica gel (20% ethyl acetate in n-heptane eluent) to give the product, (E)-ethyl-3-(4′-chloro-biphenyl-4-yl)-but-2-enoate as a colourless solid; 1.17 g (70%).

Workup

  1. customprepared
  2. stirringthe mixture stirred for 10 min
  3. temperaturethe reaction mixture heated to 80° C. for 18 h
  4. temperatureunder reflux
  5. extractionthe products extracted into ethyl acetate (2×100 ml)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customto give the crude product, which
  10. customwas purified by column chromatography on silica gel (20% ethyl acetate in n-heptane eluent)

Sources & evidence

ORD record
ord-b72479b637fd4dc08b2d0715ac1750fd
Source dataset
uspto-grants-2003_04
Patent number
US06555577B1

Reaction notes

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