2-Fluorobenzoyl chloride → 2,2'-Difluorobenzophenone

HRID 2103130Notes

Reaction equation

HRID 2103130 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+].[F:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:20]([C:19]1[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=1[F:17])=[O:21]

Participants

6

Reactant 3

HCID 98082-Fluorobenzoyl chlorideHCID 10796Cesium carbonateHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 676492,2'-DifluorobenzophenoneYield 48.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred suspension of 2-fluorobenzeneboronic acid (280 mg, 2 mmol), Cs2CO3 (1.63 g, 5 mmol) and tetrakis(triphenylphosphine)palladium(0) (40 mg, 0.02 mmol) in toluene (35 ml) under nitrogen was added dropwise 2-fluorobenzoyl chloride (634 mg, 4 mmol). The suspension was heated at 100° C. for 16 h, cooled to RT and partitioned between ethyl acetate and water. The organic layer was washed with aqueous potassium hydrogencarbonate solution, brine, dried over sodium sulfate, filtered and evaporated. Purification by flash chromatography afforded the title compound (210 mg, 46%). Colorless liquid.

Workup

  1. temperaturecooled to RT
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with aqueous potassium hydrogencarbonate solution, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-8067079da920494aba2fdc35bb991ce3
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

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