Potassium Carbonate → 3-Bromomethyl-2-methyl-4-(3-nitrophenyl)-6-phenylpyridine

HRID 981166Notes

Reaction equation

HRID 981166 reaction equation
P(Br)(Br)[Br:2].O[CH2:6][C:7]1[C:8]([CH3:28])=[N:9][C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Br:2][CH2:6][C:7]1[C:8]([CH3:28])=[N:9][C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24614Phosphorus tribromideHCID 104712403-Hydroxymethyl-2-methyl-4-(3-nitrophenyl)-6-phenylpyridine

Product 1

HCID 100913483-Bromomethyl-2-methyl-4-(3-nitrophenyl)-6-phenylpyridineYield 37.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of phosphorus tribromide (0.93 g) in tetrahydrofuran (10 ml) was dropwise added a suspension of 3-hydroxymethyl-2-methyl-4-(3-nitrophenyl)-6-phenylpyridine (1.65 g) in tetrahydrofuran (10 ml) at 5-10° C. After stirring for 1.5 hours at the same temperature, the reaction mixture was poured into icewater (20 ml), adjusted to pH 9.5 with saturated aqueous potassium carbonate and extracted with ethyl acetate (40 ml). The organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to a column chromatography on silica gel eluting with chloroform. The fractions containing the desired compound were combined and evaporated in vacuo to give 3-bromomethyl-2-methyl-4-(3-nitrophenyl)-6-phenylpyridine (0.49 g).

Workup

  1. additionthe reaction mixture was poured into icewater (20 ml)
  2. extractionextracted with ethyl acetate (40 ml)
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. additionThe fractions containing the desired compound
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-81feca37598b490aa0176a24c651b4e2
Source dataset
uspto-grants-1991_02
Patent number
US04990507

Reaction notes

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