Water → 4'-Methyl-2-nitro-1,1'-biphenyl

HRID 1909

반응식

HRID 1909 반응식
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19].O.CC(O)C>[OH-].[Na+].C1C=CC=CC=1>[CH3:10][C:1]1[CH:6]=[CH:5][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 3776IsopropanolHCID 113411-Bromo-2-nitrobenzeneHCID 79799Tolylboronic acid

생성물 1

HCID 104431944'-Methyl-2-nitro-1,1'-biphenyl수율 77.4%

시약·촉매·용매 2

HCID 241Benzene용매HCID 14798Sodium Hydroxide용매

실험 절차

A vigorously stirred mixture of 34 g (0.25 mol) of 4-tolylboronic acid and 34 g (0.17 mol) of 2-bromo-1-nitrobenzene in a mixture of 170 mL of 5N sodium hydroxide, 57 mL of water, 215 mL of 2-propanol and 1080 mL of benzene was treated with 11.9 g of (tetrakis)triphenylphosphine palladium(0). The two-phase mixture was heated at reflux for three hours. The cooled reaction mixture was filtered through Celite and the filter cake washed with fresh benzene. The organic layer was separated and washed with water (3×), dried over magnesium sulfate and filtered. The filtrate was evaporated under vacuum and the residue (46.1 g) purified by preparative high pressure liquid chromatography on silica gel, eluting with hexane/ethyl acetate (20:1), to give 28.05 g of the product.

후처리

  1. temperatureThe two-phase mixture was heated
  2. temperatureat reflux for three hours
  3. customThe cooled reaction mixture
  4. filtrationwas filtered through Celite
  5. washthe filter cake washed with fresh benzene
  6. customThe organic layer was separated
  7. washwashed with water (3×)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customThe filtrate was evaporated under vacuum
  11. customthe residue (46.1 g) purified by preparative high pressure liquid chromatography on silica gel
  12. washeluting with hexane/ethyl acetate (20:1)

출처 및 근거

ORD 기록
ord-eb2559d3fc404f17a5ecee988d37d685
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726319

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