Ammonium Chloride → 2-(3-Bromophenyl)pyridine

HRID 45454Notes

Reaction equation

HRID 45454 reaction equation
C(O[C:9]1[C:14](C=O)=[CH:13][CH:12]=[CH:11][C:10]=1[C:17]1C=[CH:21][CH:20]=[CH:19][CH:18]=1)C1C=CC=CC=1.C[Mg][Br:25].[Cl-].[NH4+:27]>O1CCCC1>[Br:25][C:14]1[CH:9]=[C:10]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][N:27]=2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 218409602-(Benzyloxy)-[1,1'-biphenyl]-3-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 111155062-(3-Bromophenyl)pyridineYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(benzyloxy)biphenyl-3-carbaldehyde (5.55 g, 20 mmol) in anhydrous tetrahydrofuran (100 mL) was stirred under nitrogen on an water bath at room temperature and 3M methyl magnesium bromide in tetrahydrofuran (10 mL, 30 mmol, 1.5 equiv.) was added. Stirring was continued at room temperature for 40 min. The reaction mixture was poured onto saturated ammonium chloride (200 mL) and extracted with ethyl acetate (2×200 mL). The organic extract was washed with water (100 mL), dried over sodium sulfate and stripped to afford pure 1 (6 g, 98%).

Workup

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. extractionThe organic extract
  3. washwas washed with water (100 mL)
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-f9f5bd13bb0c4058897facaece17fc47
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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