Ammonium Chloride → HCID 22412768, compound

HRID 1721579Notes

Reaction equation

HRID 1721579 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Br:11][C:12]1[C:13](Br)=[N:14][CH:15]=[CH:16][CH:17]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH4+].[Cl-]>C1COCC1.[Ni](Cl)Cl.C(Cl)Cl>[CH2:1]([C:15]1[CH:16]=[CH:17][C:12]([Br:11])=[CH:13][N:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 8171022,3-DibromopyridineHCID 178443577HCID 178443577, compound

Product 1

HCID 22412768HCID 22412768, compound

Reagents, catalysts & solvents 3

HCID 24385Nickel DichlorideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

30 mmol of n-octylmagnesiumbromide in 50 ml of absolute THF are added dropwise at from -15° to -10° C. to a solution of 5 g (21.1 mmol) of dibromopyridine and 0.12 g of 1,3-bis(diphenylphosphino)propane!nickel (II) chloride in 150 ml of absolute THF. The mixture is stirred at -10° C. for a further 3 hours. Saturated NH4Cl solution is subsequently added until a pH of 7 has become established, and CH2Cl2 is added for phase separation. The organic phase is separated off, the aqueous phase is extracted three times with CH2Cl2, the combined organic phases are dried over MgSO4, and the solvent is stripped off in a rotary evaporator. The crude product is chromatographed on SiO2 using CH2Cl2.

Workup

  1. customThe organic phase is separated off
  2. extractionthe aqueous phase is extracted three times with CH2Cl2
  3. dry with materialthe combined organic phases are dried over MgSO4
  4. customthe solvent is stripped off in a rotary evaporator
  5. customThe crude product is chromatographed on SiO2

Sources & evidence

ORD record
ord-df242d3b3a264c848d370d0b89777f86
Source dataset
uspto-grants-1996_04
Patent number
US05512207

Reaction notes

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