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

HRID 334258

반응식

HRID 334258 반응식
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

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 811292-Bromobenzaldehyde

생성물 1

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

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
160 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-cf70e14551404b549f65d855c83a2831
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883796B2

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