Dichloromethane → Methyl 3-methyl-4'-nitrobiphenyl-4-carboxylate

HRID 403859

반응식

HRID 403859 반응식
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=1.CC1(C)C(C)(C)OB([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)O1.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:12][C:4]1[CH:3]=[C:2]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27735554,4,5,5-Tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolaneHCID 22031226Methyl 4-bromo-2-methylbenzoate

생성물 1

HCID 59385226Methyl 3-methyl-4'-nitrobiphenyl-4-carboxylate

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
82.5 °C

실험 절차

The compound of example 219 (10 g, 0.044 mol), 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane (13.16 gm, 0.0528 mole) and Pd(dppf)Cl2:CH2Cl2 (1.07 g, 0.00132 mol) were taken in DMF (250 mL) under an argon atmosphere. To this reaction mixture, degassed 2M solution of Na2CO3 (14 g, 0.132 mol, 66.5 mL) was added. The reaction mixture was stirred at 80-85° C. for 1 to 1.5 h. After completion of the reaction, water was added and the product obtained was extracted with ether. The combined ether layer was washed with brine and dried over anhydrous Na2SO4 or MgSO4. The solvent was evaporated and the product was purified by column (silica gel, 20% ethyl acetate in petroleum ether) to obtain the title compound.

후처리

  1. additionwas added
  2. additionwas added
  3. customthe product obtained
  4. extractionwas extracted with ether
  5. washThe combined ether layer was washed with brine
  6. dry with materialdried over anhydrous Na2SO4 or MgSO4
  7. customThe solvent was evaporated
  8. customthe product was purified by column (silica gel, 20% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-f22d68aecef143089cc2c8ab56492826
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748426B2

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