Dichloromethane → HCID 22482354, compound

HRID 2181817Notes

Reaction equation

HRID 2181817 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1Br)=[O:3].[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.ClCCl.[OH-].[Na+]>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:5]1[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:4]=1[C:2](=[O:3])[CH3:1]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 27343542-Fluorophenylboronic acidHCID 227360801-(2-Bromo-5-fluorophenyl)ethan-1-one

Product 1

HCID 22482354HCID 22482354, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A stirred solution of 2-bromo-5-fluoroacetophenone (11.72 g, 54 mmol) and 2-fluorophenylboronic acid (7.55 g, 54 mmol) in tetrahydrofuran (600 mL) was treated under nitrogen with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (2.20 g, 2.69 mmol, 5 mole %) and a 5 N sodium hydroxide solution (21.6 mL, 108 mmol). The reaction was heated at 60° C. for twelve hours, cooled to room temperature, and the solvent removed in vacuo. The residue was dissolved in diethyl ether, filtered through a short column of silica gel, and the solvent evaporated in vacuo to a crude brown oil (11.72 g). The crude oil was purified by repetitive, preparative, liquid chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g), eluting with a gradient of between 3% and 10% methyl tert-butylether in hexane at a flow rate of 50 mL/min to afford, after evaporation of the solvent, the title compound as a purified, colorless oil (10.2 g, 43.9 mmol, 81%).

Workup

  1. temperaturecooled to room temperature
  2. customthe solvent removed in vacuo
  3. dissolutionThe residue was dissolved in diethyl ether
  4. filtrationfiltered through a short column of silica gel
  5. customthe solvent evaporated in vacuo to a crude brown oil (11.72 g)
  6. customThe crude oil was purified by repetitive, preparative, liquid chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g)
  7. washeluting with a gradient of between 3% and 10% methyl tert-butylether in hexane at a flow rate of 50 mL/min
  8. customto afford
  9. customafter evaporation of the solvent

Sources & evidence

ORD record
ord-47e1db58ae844137a47d4e0e61d88214
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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