Triethylamine → Biphenyl-3,5-dicarboxylic acid dimethyl ester

HRID 399848Notes

Reaction equation

HRID 399848 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])(=O)=O.OB(O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>CN(C)C=O>[C:25]1([C:7]2[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 10617248Dimethyl 5-[[(Trifluoromethyl)sulfonyl]oxy]isophthalate

Product 1

HCID 4289413Biphenyl-3,5-dicarboxylic acid dimethyl esterYield 58.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of dimethyl 5-(trifluoromethylsulfonyloxy)isophthalate (2.3 g), dihydroxy-phenylborane (1.23 g) and triethylamine (2.0 4 g) in N,N-dimethylformamide (30 ml) was heated at 100° C. and stirred for 3 hours under nitrogen. After evaporating the solvent, the residue was dissolved in a mixture of dichlomethane (100 ml) and water. The organic layer was successively washed with aqueous 10% sodium carbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from hexane to afford dimethyl 5-phenylisophthalate (1.07 g).

Workup

  1. customAfter evaporating the solvent
  2. dissolutionthe residue was dissolved in a mixture of dichlomethane (100 ml) and water
  3. washThe organic layer was successively washed with aqueous 10% sodium carbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-aba61e3b5d3249fe8a84e1659f752174
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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