Water → 2-(2-Bromo-thiophen-3-yl)-4-chloro-pyridine

HRID 910675Notes

Reaction equation

HRID 910675 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)[CH:3]=1.S1C=CC=C1B(O)O.[Br:21]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:21][C:9]1[S:10][CH:11]=[CH:12][C:8]=1[C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 27339602-Thiopheneboronic acidHCID 672422234-Chloro-2-thiophen-3-yl-Pyridine

Product 1

HCID 673883292-(2-Bromo-thiophen-3-yl)-4-chloro-pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-2-thiophen-3-yl-pyridine (755 mg, 3.9 mmol), prepared from 2-thiopheneboronic acid via the method outlined in Example 26, Step A, and N-bromosuccinimide (712 mg, 4 mmol) in DMF (6 mL) was stirred at room temperature for 8 h. The reaction mixture was poured into water and extracted with EtOAc. The organic layer was dried and concentrated to yield a residue. The residue was recrystallized from EtOH to yield 2-(2-bromo-thiophen-3-yl)-4-chloro-pyridine as a solid.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customto yield a residue
  5. customThe residue was recrystallized from EtOH

Sources & evidence

ORD record
ord-2799da07b16b442d93b9491ff104195c
Source dataset
uspto-grants-2011_09
Patent number
US08022209B2

Reaction notes

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