Chlorodiphenylphosphine → Methyl 2-diphenylphosphino-1-naphthoate

HRID 363818

반응식

HRID 363818 반응식
[C:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1OS(C(F)(F)F)(=O)=O)([O:3][CH3:4])=[O:2].Cl[P:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.Cl[Ni]Cl.[Zn]>[C:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[P:24]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([O:3][CH3:4])=[O:2]

참가 물질

6

반응물 2

HCID 66180ChlorodiphenylphosphineHCID 11034997Methyl 2-trifluoromethanesulfonyloxy-1-naphthoate

생성물 1

HCID 11760420Methyl 2-diphenylphosphino-1-naphthoate

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 24385Nickel Dichloride촉매HCID 6228Dimethylformamide용매

반응 조건

온도
108 °C

실험 절차

To a solution of 66.6 g (0.195 mol) of 1-carbomethoxy-2-(trifluoromethylsulfonyloxy)naphthalene in 450 ml DMF were added, under a nitrogen atmosphere, 3.65 g NiCl2 (dppe) (6.9 mmol) and 35 ml ClPPh2 (0.195 mol). The reaction mixture was cooled in an ice-water bath and 15 g zinc (20% excess) was added portionwise at 8°-15° C. The mixture was then heated to 108° C. for 2 hours, cooled to 50° C., filtered through silica and washed with three 20 ml portions of methanol. The filtrate was concentrated under vacuum to half of its original volume and allowed to crystallize at 0°-4° C. The product was collected and washed with methanol. Further concentration of the filtrate caused additional material to crystallize. The total yield of the title compound was 66.3 g (92%).

후처리

  1. temperatureThe reaction mixture was cooled in an ice-water bath
  2. temperaturecooled to 50° C.
  3. filtrationfiltered through silica
  4. washwashed with three 20 ml portions of methanol
  5. concentrationThe filtrate was concentrated under vacuum to half of its original volume
  6. customto crystallize at 0°-4° C
  7. customThe product was collected
  8. washwashed with methanol
  9. customto crystallize

출처 및 근거

ORD 기록
ord-836f0918e91b4c8a9c30b56a7bac7477
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05874628

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