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Potassium Phosphate, Tribasic → 4-Methyl-3-nitro-1,1'-biphenyl

HRID 912381
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HRID 912381 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.CN(C=O)C>[CH3:11][C:4]1[CH:3]=[CH:2][C:7]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]
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참가 물질

6

반응물 2

HCID 62657Potassium Phosphate, TribasicHCID 815772-Bromo-5-nitrotoluene

생성물 1

HCID 129098264-Methyl-3-nitro-1,1'-biphenyl수율 185.2%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매
HCID 6228
Dimethylformamide
용매

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온도
100 °C

실험 절차

To a DMF solution (5.0 ml) of 4-bromo-2-methyl-1-nitro-benzene (500 mg), palladium acetate (10.4 mg), S-Phos (38.0 mg) and potassium phosphate (983 mg), phenylboronic acid-pinacol ester (496 mg) was added, and then the mixture was degassed under ultrasonic irradiation. After the mixture was stirred at 100° C. for 18 hours, water (20 ml) was added, followed by extraction with ethyl acetate (20 ml×2), and the organic layer was dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off under reduced pressure, followed by purification by silica gel column chromatography (hexane/ethyl acetate=100/1), to obtain the desired compound (457 mg, 93%).

후처리

  1. customthe mixture was degassed under ultrasonic irradiation
  2. additionwater (20 ml) was added
  3. extractionfollowed by extraction with ethyl acetate (20 ml×2)
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationAfter the sodium sulfate was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customfollowed by purification by silica gel column chromatography (hexane/ethyl acetate=100/1)

출처 및 근거

ORD 기록
ord-865d8174ed804dada130866b4b33ce92
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08022205B2

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