Ammonia → 2-(Diphenylphosphanyl)-6-methoxypyridine

HRID 373760Notes

Reaction equation

HRID 373760 reaction equation
[Na].N.[C:3]1([P:9](C2C=CC=CC=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl-].[NH4+].Br[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[N:26]=1>>[C:10]1([P:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[N:26]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 2568102-Bromo-6-methoxypyridineHCID 5360545Sodium

Product 1

HCID 198020952-(Diphenylphosphanyl)-6-methoxypyridine

Conditions

Temperature
-40 °C

Procedure

2.7 g Sodium was added to 100 ml liquid ammonia at -80° C., and then 15.2 g of triphenylphosphine was added in 6 portions with stirring. The solution was slowly warmed to -40° C., kept at that temperature for 30 min, and then cooled again to -80° C. Then, 3.1 g ammonium chloride was added to the stirred solution, followed by 10.9 g of 2-bromo-6-methoxypyridine in three portions. The cooling bath was removed and the ammonia was allowed to evaporate. The residue was worked up with water/dichloromethane as described in Preparation 1. Crystallization from hexane afforded 7 g of a somewhat impure product (characterized by 31P NMR: δp =-4.4 ppm) which was used as such in the following Examples.

Workup

  1. temperaturecooled again to -80° C
  2. customThe cooling bath was removed
  3. customto evaporate
  4. customas described in Preparation 1
  5. customCrystallization from hexane
  6. customafforded 7 g of a somewhat impure product (characterized by 31P NMR: δp =-4.4 ppm) which

Sources & evidence

ORD record
ord-dcfb9a681527409ca0104f8ad564fde7
Source dataset
uspto-grants-1992_11
Patent number
US05166116

Reaction notes

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