Sodium Carbonate → (1,1'-Biphenyl)-2-carboxaldehyde

HRID 334258

反応式

HRID 334258 の反応式
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O.CCOC(C)=O.C([O-])(O)=O.[Na+].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>[C:2]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 811292-Bromobenzaldehyde

生成物 1

HCID 121052(1,1'-Biphenyl)-2-carboxaldehyde収率 75.2%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
160 °C

実験手順

2-Bromobenzaldehyde (315 μL, 2.70 mmol), phenylboronic acid (395 mg, 3.24 mmol), Pd(PPh3)4 (31 mg, 0.027 mmol) and Na2CO3 (430 mg, 4.05 mmol) were dissolved in N,N-dimethylformamide (20 mL) in a reaction vessel and refluxed at 160° C. for 6 hours. After the reaction was completed, the reaction mixture was diluted with EtOAc and saturated NaHCO3 solution was added. The organic layer obtained by extracting the aqueous layer with EtOAc was dried with anhydrous MgSO4 and then filtered. The filtrate was concentrated under reduced pressure and the concentrate was purified by column chromatography (hexane:diethyl ether=8:1) to obtain 369 mg of the target compound (2.03 mmol, 75.0%).

後処理

  1. additionwas added
  2. customThe organic layer obtained
  3. extractionby extracting the aqueous layer with EtOAc
  4. dry with materialwas dried with anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe concentrate was purified by column chromatography (hexane:diethyl ether=8:1)

出典と根拠

ORDレコード
ord-cf70e14551404b549f65d855c83a2831
出典データセット
uspto-grants-2014_11
特許番号
US08883796B2

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