Hexane → 5-Bromo-3-methyl-1-benzothiophene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10](=O)[CH3:11])=[CH:4][CH:3]=1.CCCCCC>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[S:8][CH:9]=[C:10]([CH3:11])[C:4]=2[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
Polyphosphoric acid (7 g) was added to a solution of 1-(4-bromo-phenylsulfanyl)-propan-2-one (I-24a: 2.0 g, 8.163 mmol) in toluene (10 mL) and the resulting mixture was heated to 100° C. for 5 hours. The reaction was monitored by TLC (100% hexane). The reaction mixture was cooled to room temperature, quenched with ice, basified with potassium carbonate (pH˜8) and extracted with ethyl acetate. The organic layer was concentrated to yield the crude product. Purification by column chromatography on silica gel (100% hexane) afforded 1.2 g of product (66% yield)
Workup
- temperatureThe reaction mixture was cooled to room temperature
- customquenched with ice
- extractionextracted with ethyl acetate
- concentrationThe organic layer was concentrated
- customto yield the crude product
- customPurification by column chromatography on silica gel (100% hexane)
Sources & evidence
- ORD record
- ord-1cf08af0785f4d9784603395beac3d68
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029399B2
Reaction notes
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