Benzene, 2-bromo-1,4-dimethyl- → 2,5-Dimethylbiphenyl

HRID 227871

反応式

HRID 227871 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:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=1[CH3:20]>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.C1COCC1>[CH3:20][C:14]1[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 3

HCID 11121Benzene, 2-bromo-1,4-dimethyl-HCID 66827Phenylboronic AcidHCID 522689Potassium Fluoride

生成物 1

HCID 5225062,5-Dimethylbiphenyl収率 82%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 27342152-(Di-tert-butylphosphino)biphenyl触媒HCID 8028Tetrahydrofuran溶媒

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, 0.020 mmol, 2.0 mol %), phenylboronic acid (183 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 2-bromo-p-xylene (0.138 mL, 1.0 mmol) were 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 149 mg (82%) of the title compound.

後処理

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

出典と根拠

ORDレコード
ord-0fc96fb876c146b2816281e659bf6391
出典データセット
uspto-grants-2009_07
特許番号
US07560582B2

関連ノート

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