Tetrahydrofuran → 3,4-Difluoro-4'-methoxy-1,1'-biphenyl

HRID 1510184Notes

Reaction equation

HRID 1510184 reaction equation
C1COCC1.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([Mg]Br)=[CH:10][CH:9]=1.Cl[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[CH:18]=1.[Cl-].C(C1C=CC=C(C(C)C)C=1[NH+]1CCN(C2C(C(C)C)=CC=CC=2C(C)C)C1)(C)C>CCCCCC.C1(C)C=CC=CC=1>[F:23][C:20]1[CH:21]=[C:22]([C:11]2[CH:12]=[CH:13][C:8]([O:7][CH3:6])=[CH:9][CH:10]=2)[CH:17]=[CH:18][C:19]=1[F:24]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 1365194-Chloro-1,2-difluorobenzeneHCID 184547821,3-BIS(2,6-DIISOPROPYLPHENYL)imidazoLIDINIUM-CHLORIDEHCID 178491912HCID 178491912, compound

Product 1

HCID 153121363,4-Difluoro-4'-methoxy-1,1'-biphenylYield 92%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

Using a THF solution of p-methoxyphenylmagnesium bromide (2.34 mL, 0.64 M, 1.5 mmol), 4-chloro-1,2-difluorobenzene (148.6 mg, 1.0 mmol), FeF3.3H2O (8.34 mg, 0.05 mmol) and 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride (64.1 mg, 0.15 mmol) as starting materials, the reaction was performed at a scale of 1.0 mmol at 60° C. for 24 hours, and then at 80° C. for 12 hours, in the same manner as in Example 2. After performing silica gel column chromatography (toluene=15, 30 and 50% in hexane), the above compound was obtained as a white solid (0.215 g, yield=92%, purity=>99% (GC analysis)).

Workup

  1. waitat 80° C. for 12 hours
  2. customthe above compound was obtained as a white solid (0.215 g, yield=92%, purity=>99% (GC analysis))

Sources & evidence

ORD record
ord-dc01c3c4efc44d4a8da486371b892313
Source dataset
uspto-grants-2012_07
Patent number
US08211820B2

Reaction notes

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