Phenylboronic Acid → 4-Methoxybiphenyl

HRID 1247707ノート

反応式

HRID 1247707 の反応式
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)(=O)=O.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[F-].[K+]>C1(C2(C3C=CC=CC=3)CC2(P(C(C)(C)C)C(C)(C)C)C)C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:8][CH:9]=1

参加物

6

反応物 3

HCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 5793374-Methoxyphenyl Trifluoromethanesulfonate

生成物 1

HCID 119434-Methoxybiphenyl収率 97.1%

試薬・触媒・溶媒 2

HCID 21909131Di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphane触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

Under a nitrogen atmosphere, 4-trifluoromethane-sulfonyloxyanisole (0.49 g, 1.9 mmol), phenylboronic acid (0.29 g, 2.4 mmol), potassium fluoride (0.24 g, 4.2 mmol), (π-allyl)palladium chloride (3.6 mg, 0.01 mmol), 2,2-diphenyl-1-(di-tert-butylphosphino)-1-methylcyclopropane (14.0 mg, 0.04 mmol) obtained in Example 4 and toluene (4 ml) were placed in a reaction flask and stirred for 1.5 hours at 80° C. The reaction mixture was cooled, washed with water, and dried over anhydrous magnesium sulfate. Then, the solvent was removed under reduced pressure, and the concentrate was purified by column chromatography to give the title compound (0.34 g, 96%) as white crystal.

後処理

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThen, the solvent was removed under reduced pressure
  5. customthe concentrate was purified by column chromatography

出典と根拠

ORDレコード
ord-e3fb41bd2fad4df8a86c663d5849125d
出典データセット
uspto-grants-2006_10
特許番号
US07129367B2

反応ノート

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