2-Chlorotoluene → 2,2'-Dimethylbiphenyl

HRID 1494856

반응식

HRID 1494856 반응식
[Mg].Cl[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9]>C1COCC1.Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:3][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9]

참가 물질

5

반응물 2

HCID 72382-Chlorotoluene2회HCID 5462224Magnesium

생성물 1

HCID 117972,2'-Dimethylbiphenyl

시약·촉매·용매 2

HCID 178418751HCID 178418751, 화합물촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of magnesium turnings (12.15 grams, 0.5 mole) in THF (150 mL) was added 2-chlorotoluene (50.6 grams, 0.40 mole). The mixture was refluxed for 18 hours, cooled to ambient and added dropwise to a solution of 2-chlorotoluene (44.3 grams, 0.35 mole) and bis(triphenylphosphine)-nickel (II) dichloride (2.0 grams) in THF (250 mL). The reaction mixture warmed upon mixing and was heated to reflux for 4 hours after completion of the addition. The reaction mixture was cooled and quenched by the addition of toluene (400 mL) and a saturated ammonium chloride solution (200 mL). The layers were separated and the organic phase was washed sequentially with 10 percent HCl (200 mL), water (3×100 mL), and then stripped under nitrogen to give a thick oil. The oil was distilled under vacuum to give the product as a fraction boiling in the range of 85° to 90° C. at 1 mm Hg. The yield was 43.40 grams (68 percent of theory) of 2,2'-dimethyl-1,1'-biphenyls containing 93 percent of the 2,2'-isomer and 3.5 percent of other isomers.

후처리

  1. temperatureThe mixture was refluxed for 18 hours
  2. temperaturecooled to ambient and
  3. temperatureThe reaction mixture warmed
  4. additionupon mixing
  5. temperaturewas heated
  6. temperatureto reflux for 4 hours
  7. additionafter completion of the addition
  8. temperatureThe reaction mixture was cooled
  9. customquenched by the addition of toluene (400 mL)
  10. customThe layers were separated
  11. washthe organic phase was washed sequentially with 10 percent HCl (200 mL), water (3×100 mL)
  12. customto give a thick oil
  13. distillationThe oil was distilled under vacuum
  14. customto give the product as a fraction
  15. customboiling in the range of 85° to 90° C. at 1 mm Hg

출처 및 근거

ORD 기록
ord-9af3121319fc462384088d50a294a933
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05026886

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