Bromine → 2-(5-Bromo-4-chloro-thiophen-2-yl)-6-methyl-pyridine

HRID 1432624Notes

Reaction equation

HRID 1432624 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:8]=2)[S:5][CH:6]=1.[Br:14]Br>C(Cl)Cl>[Br:14][C:6]1[S:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:8]=2)=[CH:3][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 688400882-(4-Chloro-thiophen-2-yl)-6-methyl-pyridine

Product 1

HCID 688441482-(5-Bromo-4-chloro-thiophen-2-yl)-6-methyl-pyridineYield 141%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 2-(4-chloro-thiophen-2-yl)-6-methyl-pyridine (example Rupp-96) (0.45 g, 1.45 mmol) and CH2Cl2 (10 mL) is added Br2 (0.15 mL, 2.91 mmol). The solution is warmed to ambient temperature and stirred for 1 hour. The solution is washed with sat. NaHCO3 (10 mL), sat. Na2S2O3 (10 mL), dried over MgSO4, filtered and concentrated to furnish the title compound (0.59 g, 2.04, 95%). 1H NMR (CDCl3), δ 2.55 (s, 3H), 7.05 (d, 7.9 Hz, 1H), 7.29 (s, 1H), 7.34 (d, J=7.9 Hz, 1H), 7.58 (dd, J=7.9, 7.9, 1H). LC/MS (m/z): calcd. for C10H7BrClNS (M+H)+: 288.0; found: 287.9.

Workup

  1. washThe solution is washed with sat. NaHCO3 (10 mL), sat. Na2S2O3 (10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c68f25d0a4864814a97a45864dd817ac
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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