1-Bromooctane → HCID 19387529, compound

HRID 1757354Notes

Reaction equation

HRID 1757354 reaction equation
[Mg].[CH2:2](Br)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].Br[C:12]1[CH:13]=[C:14]([F:33])[C:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:20][CH:19]=2)=[N:16][CH:17]=1>O1CCCC1.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[F:33][C:14]1[C:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:20][CH:19]=2)=[N:16][CH:17]=[C:12]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:13]=1

Participants

6

Reactant 3

HCID 81401-BromooctaneHCID 5462224MagnesiumHCID 193875465-Bromo-3-fluoro-2-(4-octyloxyphenyl)pyridine

Product 1

HCID 19387529HCID 19387529, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 178418745HCID 178418745, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

0.30 g (12.30 mmol) of magnesium and 2.16 g (11.18 mmol) of octyl bromide in 10 ml of tetrahydrofuran are used to prepare, at 50° C. for 2 hours, the solution of the Grignard compound, which is added dropwise to a solution, cooled to -10° C. of 2.13 g (5.59 mmol) of 5-bromo-3-fluoro-2-(4-octyloxyphenyl)pyridine and 0.03 g (0.06 mmol) of [1,3-bis(diphenylphosphino)propane]nickel(II) chloride in 60 ml of tetrahydrofuran, and the mixture is stirred at -10° C. for 3 hours. The mixture is subsequently partitioned between ether and aqueous ammonium chloride solution, and the organic phase is washed twice with aqueous sodium chloride solution, dried over sodium sulfate and evaporated to dryness. Chromatographic purification (silica gel/dichloromethane:hexane 7:3) gives 1.89 g of 3-fluoro-5-octyl-2-(4-octyloxyphenyl)pyridine. ##STR16## The compound has the phase sequence: X 25.5 (5) N 35 I.

Workup

  1. customto prepare, at 50° C. for 2 hours
  2. additionthe solution of the Grignard compound, which is added dropwise to a solution
  3. customThe mixture is subsequently partitioned between ether and aqueous ammonium chloride solution
  4. washthe organic phase is washed twice with aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customChromatographic purification (silica gel/dichloromethane:hexane 7:3)

Sources & evidence

ORD record
ord-1464881ae1654787abf1fbdb162a51cf
Source dataset
uspto-grants-1995_08
Patent number
US05445763

Reaction notes

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