Toluene → HCID 69286252, compound

HRID 2373129Notes

Reaction equation

HRID 2373129 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:15])[CH:9]=2)=[CH:4][CH:3]=1.[F:21][C:22]([F:33])([F:32])C1C=CC(B(O)O)=CC=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[C:58]1(C)[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=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>[CH2:17]([O:16][C:14]([C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:22]([F:33])([F:32])[F:21])([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[CH2:3][CH:4]=2)[CH:13]=[CH:12][CH:11]=1)=[O:15])[CH2:18][CH2:19][CH3:20]

Participants

9

Reactant 5

HCID 1140Toluene2×HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 69286244HCID 69286244, compound

Product 1

HCID 69286252HCID 69286252, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Finally, 3-butoxycarbonyl-4′-trifluoromethyl-p-terphenyl (CS-18) was prepared. A mixture of butyl 4′-bromobiphenyl-3-carboxylate (1.80 g, 5.4 mmol), 4-trifluoromethylbenzene boronic acid (1.08 g, 5.7 mmol), potassium carbonate (2.24 g, 16 mmol), toluene (30 mL), and 18-crown-6 (20 mg) was deaerated by sparging with nitrogen for 10 min. Tetrakis(triphenylphosphine)-palladium(0) (0.12 g, 0.11 mmol) was added, and the mixture was heated at reflux for 44 h. Additional tetrakis(triphenylphosphine)palladium(0) (0.10 g, 0.10 mmol) was added, and the reaction was continued for 24 h. The mixture was cooled to ambient, and toluene (30 mL) and water (30 mL) were added. The organic layer was separated, washed with water and with brine, dried (MgSO4), passed through short column of silica gel, and concentrated to deposit a gold solid. The product was purified by column chromatography followed by recrystallization from heptane to provide 0.96 g (45% of theory) of a white powder. 1H NMR (CDCl3): δ 1.00 (t, 3H), 1.5 (m, 2H), 1.8 (m, 2H), 4.36 (t, 2H), 7.51 (t, 1H), 7.7 (m, 8H), 7.80 (d, 1H), 8.03 (d, 1H), 8.30 (s, 1H).

Workup

  1. customby sparging with nitrogen for 10 min
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 44 h
  4. additionwere added
  5. customThe organic layer was separated
  6. washwashed with water and with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe product was purified by column chromatography
  10. customfollowed by recrystallization from heptane
  11. customto provide 0.96 g (45% of theory) of a white powder

Sources & evidence

ORD record
ord-c0e756bae9794e4cac64d366824e6898
Source dataset
uspto-grants-2008_12
Patent number
US07459263B2

Reaction notes

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