1,4-Dibromobenzene → HCID 19017168, 화합물

HRID 1728272

반응식

HRID 1728272 반응식
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][CH:4]=1.C[Si](C)(C)[O:12][C:13]1[CH:14]=[CH:15][C:16](Cl)=[N:17][CH:18]=1.C(=O)([O-])O.[Na+]>C(OCC)C.CC(P(C1C=CC=CC=1)C1C=CC=CC=1)C.C1C=CC(PC2C=CC=CC=2)=CC=1.[Cl-].[Ni].O1CCCC1>[OH:12][C:13]1[CH:14]=[CH:15][C:16]([C:3]2[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][CH:4]=2)=[N:17][CH:18]=1

참가 물질

8

반응물 4

HCID 78041,4-DibromobenzeneHCID 516892Sodium BicarbonateHCID 5462224MagnesiumHCID 19017088HCID 19017088, 화합물

생성물 1

HCID 19017168HCID 19017168, 화합물수율 67.2%

시약·촉매·용매 3

HCID 21654969Diphenylphosphane;diphenyl(propan-2-yl)phosphane;nickel;chloride촉매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A Grignard reagent solution prepared from 0.8 g of magnesium, 8.0 g of 1,4-dibromobenzene and 50 ml of tetrahydrofuran was added dropwise at 0°-5° C. within 30 minutes to a mixture of 6.6 g of 5-trimethylsilyloxy-2-chloropyridine, 75 ml of tetrahydrofuran and 0.4 g of 1,3-bis(diphenylphosphino)-propanenickel(II) chloride. The reaction mixture was stirred for 3 hours, left to stand overnight, then adjusted to pH 8 with aqueous sodium hydrogen carbonate solution and diluted with diethyl ether. The organic phase was washed neutral with water, dried over sodium sulfate and concentrated. Chromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 4:1) yielded 5.5 g of 5-hydroxy-2-(4-bromophenyl)-pyridine.

후처리

  1. waitleft
  2. waitto stand overnight
  3. washThe organic phase was washed neutral with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customChromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 4:1)

출처 및 근거

ORD 기록
ord-7bf43c9387e74ea98eb45762e01f3f7d
출처 데이터셋
uspto-grants-1994_07
특허 번호
US05326497

연결된 노트

불러오는 중…