Phenylboronic Acid → 3-Phenyl-2-furoic acid

HRID 472675

반응식

HRID 472675 반응식
Br[C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([OH:9])=[O:8].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.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:10]1([C:2]2[CH:6]=[CH:5][O:4][C:3]=2[C:7]([OH:9])=[O:8])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 6054793-Bromofuran-2-carboxylic acid

생성물 1

HCID 88997083-Phenyl-2-furoic acid수율 70%

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

실험 절차

To 3-bromo-2-furancarboxylic acid (540 mg, 2.8 mmol dissolved in DME (105 ml)) was added of (Ph3P)4Pd (936 mg, 0.81 mmol), and the resulting solution was stirred at room temperature for 15 min. The mixture was treated with 500 mg (3.0 mmol) of benzene boronic acid, an aqueous solution of 2M NaHCO3 (4 mmol) and heated to reflux for 10 hours. After cooling to room temperature, the solvent was partially removed under reduced pressure, and the resulting mixture was extracted twice with diethyl ether. The water layer was acidified with 10% HCl and extracted with ethyl acetate (5 times). The combined organic layers were washed with brine, dried (Na2SO4), and evaporated under reduced pressure. The residue was crystallized from a mixture of n-hexane/ethyl acetate (about 8:2) to give the title compound. Yield: 70%.

후처리

  1. temperatureto reflux for 10 hours
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was partially removed under reduced pressure
  4. extractionthe resulting mixture was extracted twice with diethyl ether
  5. extractionextracted with ethyl acetate (5 times)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customThe residue was crystallized from a mixture of n-hexane/ethyl acetate (about 8:2)

출처 및 근거

ORD 기록
ord-767f477d260449c38f28649c1fde450a
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633215B2

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