Bromine → 2-Bromo-5,6-dihydrothieno(2,3-c)pyridin-7(4H)-one
Reaction equation
[S:1]1[C:5]2[C:6](=[O:10])[NH:7][CH2:8][CH2:9][C:4]=2[CH:3]=[CH:2]1.[Br:11]Br>CC(O)=O.O>[Br:11][C:2]1[S:1][C:5]2[C:6](=[O:10])[NH:7][CH2:8][CH2:9][C:4]=2[CH:3]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Dissolve 5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (4.80 g, 31.37 mmol) in HOAc (40 mL) and water (30 mL). Cool to 0° C. and add Br2 (1.8 mL, 34.51 mmol) dropwise. Stir the reaction at 0° C. for 1 h. Dilute the reaction mixture with water (100 mL) and extract with EtOAc (3×100 mL). Wash the combined organic layers with 5% Na2SO3 (2×50 mL), saturated NaHCO3 (2×100 mL), dry over Na2SO4, filter, and concentrate to give 6.198 g (85%) of the title compound. MS/ES m/z (81Br) 233.9 [M+H]+; 1H-NMR (400 MHz, CDCl3) δ 2.87 (t, J=6.9 Hz, 2H), 3.59 (t, J=6.9 Hz, 2H), 6.21 (bs, 1H), 6.93 (s, 1H).
Workup
- customthe reaction at 0° C. for 1 h
- extractionextract with EtOAc (3×100 mL)
- washWash the combined organic layers with 5% Na2SO3 (2×50 mL), saturated NaHCO3 (2×100 mL)
- dry with materialdry over Na2SO4
- filtrationfilter
- concentrationconcentrate
Sources & evidence
- ORD record
- ord-9bac0c50a7b2490b9f8646b0111f698e
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263772B2
Reaction notes
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