4,4'-Difluorobenzophenone → HCID 2960505, compound

HRID 1667095Notes

Reaction equation

HRID 1667095 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[O:21])=[CH:16][CH:15]=1>O1CCCC1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[OH:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 95824,4'-DifluorobenzophenoneHCID 142684-BromopyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 2960505HCID 2960505, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-bromopyridine (0.78 g, 5.0 mmol) in tetrahydrofuran (5 mL) was added isopropylmagnesium chloride (2.0 Min tetrahydrofuran, 2.5 mL, 5.0 mmol) via syringe under nitrogen at room temperature. The reaction mixture was stirred for one hour. To the reaction mixture was then added bis(4-fluorophenyl)methanone (0.98 g, 4.5 mmol) dissolved in tetrahydrofuran (7 mL) via syringe. The reaction mixture was stirred overnight, quenched with a saturated aqueous solution of ammonium chloride (10 mL), and extracted with diethyl ether. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with 5% methanol/dichloromethane gave bis(4-fluorophenyl)(pyridin-4-yl)methanol on (0.73 g, 2.45 mmol).

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. customquenched with a saturated aqueous solution of ammonium chloride (10 mL)
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washSilica gel chromatography eluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-faabd72ae8674d4e8f2eb7be95440e9a
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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