Phenylboronic Acid → 4-Methoxybiphenyl

HRID 1247707노트

반응식

HRID 1247707 반응식
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

참가 물질

6

반응물 3

HCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 5793374-Methoxyphenyl Trifluoromethanesulfonate

생성물 1

HCID 119434-Methoxybiphenyl수율 97.1%

시약·촉매·용매 2

HCID 21909131Di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphane촉매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e3fb41bd2fad4df8a86c663d5849125d
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129367B2

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