Phenylboronic Acid → 2,6-Dimethylbiphenyl

HRID 1354952

反応式

HRID 1354952 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[C:18]([CH3:19])=[CH:17][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][CH:17]=[C:18]([CH3:19])[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 66827Phenylboronic AcidHCID 684712-Bromo-m-xyleneHCID 522689Potassium Fluoride

生成物 1

HCID 1380902,6-Dimethylbiphenyl収率 79%

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-m-xylene (0.144 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 65° C. 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 144 mg (79%) 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-3abb1d1ece1a4d568e9cffa9022ef06f
出典データセット
uspto-grants-2007_05
特許番号
US07223879B2

関連ノート

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