Dimethyl Sulfoxide → 3-Bromo-5-(methylthio)benzoic acid
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9](Br)[CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:12][S:13]C.[Na].CS(C)=O>O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:13][CH3:12])[CH:10]=1)[C:5]([OH:7])=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 3,5-dibromobenzoic acid (2.5 g, 8.9 mmol), sodium methyl sulfide (1.4 g, 20 mmol), and dimethyl sulfoxide (10 mL) was sealed in a microwave tube and heated with an oil bath at 100° C. for 4 h. TLC indicated completion of the reaction. The reaction mixture was poured into water and extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated. The residue was used for the next step reaction without purification. 1H NMR (400 MHz, CDCl3): δ 7.97 (t, 1H, J=1.6 Hz), 7.87 (t, 1H, J=1.6 Hz), 7.57 (t, 1H, J=1.6 Hz), 2.53 (s, 3H).
Workup
- customwas sealed in a microwave tube
- customcompletion of the reaction
- extractionextracted with EtOAc (3×50 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe residue was used for the next step reaction without purification
Sources & evidence
- ORD record
- ord-f3447b433277421192915e041a77ac7f
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
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