1-Bromo-4-iodobenzene → 1-Benzyl-4-bromobenzene

HRID 129796

반응식

HRID 129796 반응식
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1>C1COCC1>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

참가 물질

4

반응물 2

HCID 115221-Bromo-4-iodobenzeneHCID 178418336HCID 178418336, 화합물

생성물 1

HCID 2360001-Benzyl-4-bromobenzene수율 80.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred solution of 21 mL (42 mmol, 2.0M in THF) of benzylmagnesium chloride at room temperature under nitrogen was added a solution of 6.80 g (50.0 mmol) of thrice-fused zinc chloride in 0 50 mL of THF. The resulting tan slurry was stirred for 1 hour. To this slurry was added 10.0 g (35.3 mmol) 1-bromo-4-iodobenzene and 450 mg (0.4 mmol) of tetrakis(tri-phenylphosphine)palladium in 30 mL of THF. The reaction was stirred at room temperature for 16 hours and then quenched with 50 mL of 2M hydro-chloric acid. The mixture was extracted thrice with hexanes, the extracts combined, washed once with saturated sodium bicarbonate solution and once with 10% sodium thiosulfate. The organic extract was dried (MgSO4) and evaporated. The crude product was purified by flash chromatography on silica gel (5×25 cm column, hexanes as elutent) to give 7.05 g (80%) of title compound as a colorless oil.

후처리

  1. stirringThe reaction was stirred at room temperature for 16 hours
  2. customquenched with 50 mL of 2M hydro-chloric acid
  3. extractionThe mixture was extracted thrice with hexanes
  4. washwashed once with saturated sodium bicarbonate solution and once with 10% sodium thiosulfate
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. customevaporated
  8. customThe crude product was purified by flash chromatography on silica gel (5×25 cm column, hexanes as elutent)

출처 및 근거

ORD 기록
ord-83366d45be734b0e9f222819584de400
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470845

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