4'-Bromoacetanilide → N-Acetyl-4-aminobiphenyl

HRID 1354950Notes

Reaction equation

HRID 1354950 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].[K+].Br[C:13]1[CH:22]=[CH:21][C:16]([NH:17][C:18](=[O:20])[CH3:19])=[CH:15][CH:14]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>[C:18]([NH:17][C:16]1[CH:21]=[CH:22][C:13]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:14][CH:15]=1)(=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 76834'-BromoacetanilideHCID 66827Phenylboronic AcidHCID 522689Potassium Fluoride

Product 1

HCID 19998N-Acetyl-4-aminobiphenylYield 86.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 27342152-(Di-tert-butylphosphino)biphenylCatalyst

Procedure

An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol %), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol %), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4′-bromoacetanilide (214 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 182 mg (86%) of the title compound.

Workup

  1. customAn oven dried resealable Schlenk tube
  2. customwas evacuated
  3. customThe tube was evacuated
  4. additionwas added through a rubber septum
  5. customThe tube was sealed with a teflon screwcap
  6. customhad been completely consumed
  7. additionThe reaction mixture was then diluted with ether (30 mL)
  8. filtrationfiltered through celite
  9. concentrationconcentrated
  10. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-b62b4ec88f7c45bcb3e7740fbf34a7a8
Source dataset
uspto-grants-2007_05
Patent number
US07223879B2

Reaction notes

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