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

HRID 910674Notes

Reaction equation

HRID 910674 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.O.C(Cl)[Cl:23]>>[Cl:23][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

5

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 27339602-Thiopheneboronic acidHCID 672422234-Chloro-2-thiophen-3-yl-Pyridine

Product 1

HCID 673882752-(2-Chloro-thiophen-3-yl)-4-chloro-pyridine

Procedure

To a solution of 4-chloro-2-thiophen-3-yl-pyridine (410 mg, 2.1 mmol), prepared as described in Example 26, Step A, using 2-thiopheneboronic acid, in CH2Cl2 (10 mL), was added SO2Cl2 (1 M in CH2Cl2, 3 mL). The resulting mixture was stirred at room temperature for 8 h, then was poured into water and extracted with CH2Cl2. The organic layer was dried and concentrated to yield a residue. The residue was purified by preparative TLC (hexanes/EtOAc) to yield 2-(2-chloro-thiophen-3-yl)-4-chloro-pyridine.

Workup

  1. extractionextracted with CH2Cl2
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customto yield a residue
  5. customThe residue was purified by preparative TLC (hexanes/EtOAc)

Sources & evidence

ORD record
ord-a81592eec31b4b928beb0a15b97ee6f8
Source dataset
uspto-grants-2011_09
Patent number
US08022209B2

Reaction notes

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