Tributylphosphine → HCID 83392983, compound

HRID 2283388Notes

Reaction equation

HRID 2283388 reaction equation
[Cl:1][C:2]1[C:7]([C:8](Cl)=[O:9])=[C:6]([F:11])[C:5]([CH3:12])=[CH:4][CH:3]=1.C(P(CCCC)CCCC)CCC.[C:26]1([Mg]Br)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1>[Cl:1][C:2]1[C:7]([C:8]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:9])=[C:6]([F:11])[C:5]([CH3:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 27736716-Chloro-2-fluoro-3-methylbenzoyl chlorideHCID 178418255HCID 178418255, compound

Product 1

HCID 83392983HCID 83392983, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step 1 To a solution of 6-chloro-2-fluoro-3-methyl-benzoyl chloride (2.07 g, 10.0 mmol) in anhydrous tetrahydrofuran (50 ml), stirred under nitrogen in an acetonitrile/CO2 bath, was added tributyl phosphine (2.75 ml, 11.0 mmol). The mixture was stirred for 15 minutes before phenylmagnesium bromide (3M in diethyl ether, 3.67 ml, 11.0 mmol) was added dropwise. After 45 minutes, the reaction was quenched by addition of hydrochloric acid (2N, 50 ml). The mixture was extracted with ethyl acetate. The organic liquors were washed with sodium bicarbonate solution and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by silica chromatography eluting with 0-10% diethyl ether/petroleum ether furnishing (6-chloro-2-fluoro-3-methyl-phenyl)-phenyl-methanone as a yellow oil that slowly crystallised (1.12 g, ca. 80% pure). Trituration with petroleum ether produced an analytically pure sample. MS: [M+H]+ 249

Workup

  1. additionwas added dropwise
  2. customthe reaction was quenched by addition of hydrochloric acid (2N, 50 ml)
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic liquors were washed with sodium bicarbonate solution and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica chromatography
  8. washeluting with 0-10% diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-4741f7c7ec5c494f9265977eb32611f2
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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