Bromine → 2-Bromo-7-chlorothieno[3,2-b]pyridine

HRID 2193677Notes

Reaction equation

HRID 2193677 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.[Li]CCCC.[Br:16]Br>C1COCC1>[Br:16][C:9]1[S:10][C:3]2[C:4](=[N:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH:8]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 112752517-Chlorothieno[3,2-b]pyridineHCID 178418339Butyllithium

Product 1

HCID 183827742-Bromo-7-chlorothieno[3,2-b]pyridineYield 755.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2 (10.12 g, 5.59 mmol) in dry THF (200 ml) at −78° C. was added n-BuLi (24 ml, 76.7 mmol, 2.5 M solution in hexanes) and the resultant suspension was stirred for 15 minutes. Bromine (18.9 g, 120 mmol) was added slowly and the reaction mixture was stirred for additional 30 minutes, quenched with water and diluted with EtOAc. The organic phase was separated and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography (eluent EtOAc/Hexane 9:1) afforded title compound 49 (10.5 g, 71% yield) as a yellow solid. 1H NMR (CDCl3) δ (ppm): 8.62 (d, J=5.09 Hz, 1H), 7.92 (s, 1H), 7.59 (d, J=5.09 Hz, 1H).

Workup

  1. customquenched with water
  2. additiondiluted with EtOAc
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography (eluent EtOAc/Hexane 9:1)

Sources & evidence

ORD record
ord-de2296a2e39b410581c7d25c27f90cf2
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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