Potassium Phosphate, Tribasic → 4-Methyldibenzo[b,d]furan

HRID 717990

반응식

HRID 717990 반응식
I[C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:23]B1OB(C)OB(C)O1>C1(C)C=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[CH3:23][C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 4582574-IododibenzofuranHCID 574072Trimethylboroxine

생성물 1

HCID 434894-Methyldibenzo[b,d]furan수율 554.3%

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매HCID 962Water용매2회HCID 1140Toluene용매

실험 절차

4-Iododibenzo[b,d]furan (10 g, 34.0 mmol) and potassium phosphate (23.49 g, 102 mmol) were dissolved in 200 mL of toluene and 20 mL of water. The reaction was purged with nitrogen for 20 minutes and then 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (5.34 mL, 5.94 mmol), Pd2(dba)3 (0.311 g, 0.34 mmol) and S-Phos (0.558 g, 1.36 mmol) were added. The reaction was refluxed for 18 hours. After allowing the reaction to cool to room temperature, 100 mL of water was added, the organic and aqueous layers were separated, and the aqueous layer extracted twice with 100 mL of toluene. The organic layers were passed through a plug of silica gel, eluting with DCM. After evaporation of the solvent, the crude product was subjected to column chromatography (SiO2, 3% ethyl acetate in hexane to 5% ethyl acetate in hexane, v/v) to yield 6 g (96.7%) pure product which was confirmed GC.

후처리

  1. customThe reaction was purged with nitrogen for 20 minutes
  2. temperatureThe reaction was refluxed for 18 hours
  3. customthe reaction
  4. customthe organic and aqueous layers were separated
  5. extractionthe aqueous layer extracted twice with 100 mL of toluene
  6. washeluting with DCM
  7. customAfter evaporation of the solvent

출처 및 근거

ORD 기록
ord-7cb3671deae64fd89ec0c2f9db78670f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193745B2

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