Sodium Carbonate → Ethyl 2'-chloro-4'-(trifluoromethyl)[1,1'-biphenyl]-3-acetate

HRID 628474Notes

Reaction equation

HRID 628474 reaction equation
I[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>O>[Cl:14][C:15]1[CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=[CH:17][C:16]=1[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:3]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2783251[2-Chloro-4-(trifluoromethyl)phenyl]boronic acidHCID 57581611Ethyl 2-(3-iodophenyl)acetate

Product 1

HCID 66973842Ethyl 2'-chloro-4'-(trifluoromethyl)[1,1'-biphenyl]-3-acetateYield 49.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 3-iodophenylacetate (2.90 g), 2-chloro-4-(trifluoromethyl)phenyl boronic acid (3.3 g), 2M aqueous sodium carbonate solution (5 mL), dioxane (10 mL) and dichloro-bis(triphenylphosphine)palladium(II) (350 mg) were heated at 80° C. for 30 min with stirring. The reaction mixture was then cooled, poured into water, extracted with ethyl acetate, and the organic layer was separated and concentrated under vacuum in the presence of Celite® to a solid residue. This solid residue was purifed by medium pressure liquid chromatography on silica gel eluting with a gradient of ethyl acetate in hexanes to yield 1.7 g of the title compound. 1H NMR (CDCl3) δ 7.14 (s, 1H), 7.56 (d, 1H) 7.30-7.45 (m, 5H), 4.77 (q, 2H), 3.67 (s, 2H), 1.26 (t, 3H).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionextracted with ethyl acetate
  3. customthe organic layer was separated
  4. concentrationconcentrated under vacuum in the presence of Celite® to a solid residue

Sources & evidence

ORD record
ord-c3372ef86a244da295e2f6154242b659
Source dataset
uspto-grants-2016_04
Patent number
US09314025B2

Reaction notes

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