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

HRID 496942

反応式

HRID 496942 の反応式
[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]

参加物

6

反応物 3

HCID 76834'-BromoacetanilideHCID 66827Phenylboronic AcidHCID 522689Potassium Fluoride

生成物 1

HCID 19998N-Acetyl-4-aminobiphenyl収率 86.2%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 27342152-(Di-tert-butylphosphino)biphenyl触媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8348f432382b4fea94f28602a0cba331
出典データセット
uspto-grants-2005_09
特許番号
US06946560B2

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