1,2-Dimethoxyethane → 4-Hydroxy-(1,1'-biphenyl)-3-carbaldehyde

HRID 1514007

반응식

HRID 1514007 반응식
Br[C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH:7]([C:6]1[CH:9]=[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:3]=[CH:4][C:5]=1[OH:10])=[O:8]

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 728635-Bromosalicylaldehyde

생성물 1

HCID 122646584-Hydroxy-(1,1'-biphenyl)-3-carbaldehyde수율 78.3%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

In an atmosphere of argon, 496 g (2.46 mol) of 5-bromosalicylaldehyde, 361 g (2.96 mol) of phenylboronic acid, 57 g (49.0 mmol) of tetraxis(triphenylphosphine)palladium(0), 8.6 L of DME and 784 g of sodium carbonate/3.7 L of water were charged, and subjected to heating under reflux with stirring for 17 hours. After cooling the resultant to room temperature, 3 L of toluene was added, and then an aqueous layer was removed. An organic layer was washed with water, and dried with magnesium sulfate. The solvent was distilled off under a reduced pressure. The crystals were purified by silica gel chromatography, whereby 382 g of 3-formyl-4-hydroxybiphenyl was obtained (yield: 78%).

후처리

  1. temperatureto heating
  2. temperatureunder reflux
  3. customan aqueous layer was removed
  4. washAn organic layer was washed with water
  5. dry with materialdried with magnesium sulfate
  6. distillationThe solvent was distilled off under a reduced pressure
  7. customThe crystals were purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-2177e73fe4ce40178b81097a8b81cb95
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08221907B2

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