Methanol → 1-(4'-Chloro-4-nitro-biphen-2-yl)-ethanone

HRID 1788583Notes

Reaction equation

HRID 1788583 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12].[Cl:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.CO.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[C:3]([C:11](=[O:13])[CH3:12])=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 742994-Chlorophenylboronic acidHCID 516892Sodium BicarbonateHCID 234021201-(2-Bromo-5-nitrophenyl)ethanone

Product 1

HCID 860270631-(4'-Chloro-4-nitro-biphen-2-yl)-ethanone

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

1-(2-Bromo-5-nitro-phenyl)-ethanone (1 g, 4 mmol; prepared similarly to the procedure described in Meisenheimer, J., Zimmermann P., and v. Kummer, U. Ann. der. Chem. 446, pp. 205-228), p-Chlorophenylboronic acid (768 mg, 1.2 eq.), and tetrakis(triphenylphosphine)-palladium(0) (473 mg, 0.1 eq.), were dissolved in 25 mL toluene, 6 mL methanol and 2.5 mL sat. sodium bicarbonate solution. After degassing/sonicating the solution, the sealed reaction vessel was heated to 80° C. overnight. The cooled solution was separated between ethyl acetate and water; the aqueous phase extracted two more times with ethyl acetate, and the organic fractions were combined, dried with sodium sulfate and evaporated. Silica gel chromatography (4:1 hexanes/ethyl acetate) gave 1-(4′-chloro-4-nitro-biphen-2-yl)-ethanone (962 mg).

Workup

  1. customprepared similarly to the procedure
  2. customAfter degassing/sonicating the solution
  3. customthe sealed reaction vessel
  4. customThe cooled solution was separated between ethyl acetate and water
  5. extractionthe aqueous phase extracted two more times with ethyl acetate
  6. dry with materialdried with sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-db6a3b04c04d45caaa23c9fa24f0ced6
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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