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

HRID 1531296Notes

Reaction equation

HRID 1531296 reaction equation
Br[C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].P([O-])([O-])([O-])=O.[K+].[K+].[K+].ClCCl.[F:24][C:25]([F:36])([F:35])[C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:12][C:11]1[CH:10]=[CH:9][CH:8]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[C:2]=1[C:29]1[CH:30]=[CH:31][C:26]([C:25]([F:36])([F:35])[F:24])=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 10823279Methyl 2-Bromo-3-methylbenzoate

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of methyl 2-bromo-3-methylbenzoate (22.33 g, 97.5 mmol), potassium phosphate (82.8 g, 390 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloro palladium (II), complex with dichloromethane (1:1) (3.98 g, 4.87 mmol), and p-trifluoromethylphenylboronic acid (22.2 g, 117 mmol) in 500 mL of DME is degassed and refluxed under an atmosphere of argon overnight. The mixture is concentrated, poured into water and extracted with ethyl acetate. The combined organic extracts are washed with brine, dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue is purified by silica gel chromatography eluting with ethyl acetate/toluene (1:9) to give methyl 6-methyl4′-trifluoromethyl-biphenyl-2-carboxylate.

Workup

  1. customis degassed
  2. temperaturerefluxed under an atmosphere of argon overnight
  3. concentrationThe mixture is concentrated
  4. additionpoured into water
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts are washed with brine
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue is purified by silica gel chromatography
  11. washeluting with ethyl acetate/toluene (1:9)

Sources & evidence

ORD record
ord-9a969a5219fd46f5a11ba15d1de3032c
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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