1,4-Dibromobenzene → HCID 19017168, compound

HRID 1728272Notes

Reaction equation

HRID 1728272 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

HCID 19017168HCID 19017168, compoundYield 67.2%

Reagents, catalysts & solvents 3

HCID 21654969Diphenylphosphane;diphenyl(propan-2-yl)phosphane;nickel;chlorideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-7bf43c9387e74ea98eb45762e01f3f7d
Source dataset
uspto-grants-1994_07
Patent number
US05326497

Reaction notes

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