Potassium Carbonate → 6-Methyl-3'-nitrobiphenyl-3-carboxylic acid

HRID 1894890

반응식

HRID 1894890 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)O1.I[C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:23]([OH:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.C(O)CCC.O.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>[CH3:29][C:28]1[C:27]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1

참가 물질

9

반응물 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 6216403-Iodo-4-methylbenzoic acidHCID 112651643-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene

생성물 1

HCID 690465616-Methyl-3'-nitrobiphenyl-3-carboxylic acid수율 88.9%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 2631-Butanol용매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
20 °C

실험 절차

4,4,5,5-Tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane (5.16 g, 0.0207 mol) was mixed with 3-iodo-4-methylbenzoic acid (4.94 g, 0.0188 mol), and potassium carbonate (10.4 g, 0.0753 mol) in toluene (100 mL), 1-butanol (20 mL) and water (15 mL) and the resulting mixture was degassed by sparging nitrogen through it. To the reaction was added tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.00091 mol). The mixture was stirred rapidly and was heated to reflux for 1.5 hour. LCMS analysis showed the reaction to be complete, M+H 258. The mixture was then cooled to 20° C. The aqueous layer was discarded. To the organic layer was added saturated NaHCO3. The toluene layer was extracted with aqueous sodium bicarbonate, then discarded. The aqueous sodium bicarbonate and alcohol layers were combined, then acidified to pH 2.5 with HCl. A white solid precipitated and was separated by filtration, rinsed with water, and air dried to give 4.3 g of the product. The filtrate contained only a trace of product.

후처리

  1. customthe resulting mixture was degassed
  2. customby sparging nitrogen through it
  3. temperaturewas heated
  4. temperatureto reflux for 1.5 hour
  5. customthe reaction
  6. extractionThe toluene layer was extracted with aqueous sodium bicarbonate
  7. customA white solid precipitated
  8. customwas separated by filtration
  9. washrinsed with water, and air
  10. customdried

출처 및 근거

ORD 기록
ord-9216bc0231574142a54c7621de5047a2
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513270B2

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