Phenylboronic Acid → HCID 22556974、化合物

HRID 983805ノート

反応式

HRID 983805 の反応式
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

参加物

7

反応物 2

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

生成物 1

HCID 22556974HCID 22556974、化合物収率 50.5%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒HCID 11430Potassium Carbonate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cf82e8c79a044ef2bbf0875d9021a4bf
出典データセット
uspto-grants-2005_03
特許番号
US06867200B1

反応ノート

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