Phenylboronic Acid → HCID 22556974, 화합물

HRID 983805노트

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HRID 983805 반응식
Br[C:2]1[C:3]([OH:11])=[C:4]([CH:7]=[C:8]([CH3:10])[CH:9]=1)[CH:5]=[O:6].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CCOCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:11][C:3]1[C:4]([CH:5]=[O:6])=[CH:7][C:8]([CH3:10])=[CH:9][C:2]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

7

반응물 2

HCID 66827Phenylboronic AcidHCID 27570153-bromo-2-hydroxy-5-methylbenzaldehyde

생성물 1

HCID 22556974HCID 22556974, 화합물수율 50.5%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매HCID 11430Potassium Carbonate용매

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온도
80 °C

실험 절차

A mixture of 3-bromo-2-hydroxy-5-methylbenzaldehyde (0.30 g, 1.40 mmoles), phenyl boronic acid (0.20 g, 1.67 mmoles) and tetrakis(triphenylphosphine)palladium(0) (81 mg, 0.07 mmoles) in toluene (10 ml) and 2M K2CO3 (3 ml) was heated to 80° C. for 2 hr. The reaction mixture was cooled to ambient temperature, diluted with ether (100 ml) and washed with NaHCO3. The organic layer was dried (MgSO4), filtered and concentrated to yield a residue which was purified using flash chromatography (10% ethyl acetate/hexanes) to yield 0.15 g (49%) of the title compound as a yellow oil.

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. washwashed with NaHCO3
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a residue which
  7. customwas purified

출처 및 근거

ORD 기록
ord-cf82e8c79a044ef2bbf0875d9021a4bf
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06867200B1

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