Ethyl Acetate → 2'-Chloro[1,1'-biphenyl]-4-carbaldehyde

HRID 1394158

반응식

HRID 1394158 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Cl:8].[CH:9]([C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)=[O:10].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.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>[CH:9]([C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[Cl:8])=[CH:13][CH:12]=1)=[O:10]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 127541-Bromo-2-chlorobenzeneHCID 5910734-Formylphenylboronic Acid

생성물 1

HCID 13944002'-Chloro[1,1'-biphenyl]-4-carbaldehyde

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

To a solution of 2-bromochlorobenzene (0.24 mL, 2 mmol) and 4-formylbenzeneboronic acid (0.35 g, 2.2 mmol) in toluene (20 mL) were added 2M aq. sodium carbonate (2.6 mL) followed by (Ph3P)4Pd (0.34 g, 0.3 mmol). The resulting reaction mixture was refluxed for 3 h, cooled and diluted ethyl acetate. The organic phase was washed with water, saturated aq. sodium bicarbonate, brine and dried over sodium sulfate. The filtrate was concentrated in vacuo and the residue obtained was purified by chromatography (hexane:ethyl acetate; 4:1) to yield the title product.

후처리

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 3 h
  3. temperaturecooled
  4. washThe organic phase was washed with water, saturated aq. sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue obtained
  8. customwas purified by chromatography (hexane:ethyl acetate; 4:1)

출처 및 근거

ORD 기록
ord-c73cff83589e435d93d15875f07dee8c
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348348B2

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