Tetrahydrofuran → Methyl 6-methyl-4'-trifluoromethylbiphenyl-2-carboxylate

HRID 1531299Notes

Reaction equation

HRID 1531299 reaction equation
FC(F)(F)S(O[C:7]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])(=O)=O.C(=O)([O-])[O-].[K+].[K+].O1CCCC1.[F:31][C:32]([F:43])([F:42])[C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:17][C:16]1[CH:15]=[CH:14][CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]=1[C:36]1[CH:37]=[CH:38][C:33]([C:32]([F:43])([F:42])[F:31])=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 224988133-Methyl-2-(trifluoromethylsulfonyloxy)benzoic acid methyl ester

Product 1

HCID 11833278Methyl 6-methyl-4'-trifluoromethylbiphenyl-2-carboxylate

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

To a solution of methyl 2-trifluoromethanesulfonyloxy-3-methylbenzoate (900 g, in toluene), potassium carbonate (629.6 g), tetrahydrofuran (2700 mL) and deionized water (5400 mL) under nitrogen is added tetrakis (triphenylphosphine) palladium (0) (104.6 g). To this is added the above solution of p-trifluoromethylphenylboronic acid and the mixture is heated at reflux for 2 days. The reaction mixture is filtered and evaporated to dryness. The residue is partitioned between water and ethyl acetate. The ethyl acetate layer is separated and evaporated to dryness. The residue is taken up in heptane-ethyl acetate (9:1), the mixture is filtered and the filtrate is evaporated to dryness to give methyl 6-methyl-4′-trifluoromethylbiphenyl-2-carboxylate as an oil.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 2 days
  3. filtrationThe reaction mixture is filtered
  4. customevaporated to dryness
  5. customThe residue is partitioned between water and ethyl acetate
  6. customThe ethyl acetate layer is separated
  7. customevaporated to dryness
  8. filtrationthe mixture is filtered
  9. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-19e7aae20f2442e2935a07b06ac4b2a6
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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