Water → 4-(Trifluoromethoxy)-4'-methoxy-1,1'-biphenyl

HRID 250526Notes

Reaction equation

HRID 250526 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCCC1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 5843192-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 111732034-(Trifluoromethoxy)-4'-methoxy-1,1'-biphenylYield 193.9%

Reagents, catalysts & solvents 2

HCID 178477754HCID 178477754, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-bromo-4-(trifluoromethoxy)benzene (0.90 g, 3.7 mmol) in tetrahydrofuran (20 ml) was added a solution of 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.36 g, 1.54 mmol) in tetrahydrofuran (10 ml), potassium carbonate (0.42 g, 3.0 mmol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (40 mg, 0.077 mmol) and water (0.20 ml) and the mixture refluxed under nitrogen for 19 h. The reaction mixture was tipped into water (150 ml) and extracted with ether (2×50 ml), the ether extract then dried (MgSO4) and evaporated to give a tan semi-solid (0.801 g). Purification by column chromatography (silica gel, 4:1 hexane/chloroform) afforded 4-methoxy-4′-(trifluoromethoxy)-1,1′-biphenyl (36) as a white solid (0.33 g, 80%). 1H nmr (CDCl3, 300 MHz) 3.86, s, 4-OMe; 6.99, d (8.7 Hz), H3,5; 7.26, d (8.1 Hz), H3′,5′; 7.49, d (8.7 Hz), H2,6 or H2′,6′; 7.55, d (8.7 Hz), H2′,6′ or H2,6. APCI (+ve) MS m/z 268 (M+, 80%).

Workup

  1. temperaturethe mixture refluxed under nitrogen for 19 h
  2. extractionextracted with ether (2×50 ml)
  3. extractionthe ether extract
  4. dry with materialthen dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-264939122f4147899685375cb376787d
Source dataset
uspto-grants-2011_01
Patent number
US07863313B2

Reaction notes

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