N,N-Diethylaniline → 5-Bromo-2-methyl-1-benzothiophene
Reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([S:6][CH2:7][C:8](Cl)=C)=[CH:4][CH:3]=1.[CH2:13](N(CC)C1C=CC=CC=1)C>CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:6][C:7]([CH3:8])=[CH:13][C:11]=2[CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
According to the procedure of W. K. Anderson, J. Chem. Soc., Perkin, 1, 1 (1976), a mixture of 3-(4-bromothiophenoxy)-2-chloro-1-propene (37.4 g, 0.142 mol) and N,N-diethylaniline (180 mL) was heated to 210°-215° C. for 2 days, cooled, and diluted with ether. The ethereal layer was washed with 10% HCl (3×200 mL), dried (MgSO4), and concentrated. Purification by column chromatography (eluant: hexane) gave 15.0 g (46%) of product as a white solid.
Workup
- temperaturewas heated to 210°-215° C. for 2 days
- temperaturecooled
- washThe ethereal layer was washed with 10% HCl (3×200 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customPurification by column chromatography (eluant: hexane)
Sources & evidence
- ORD record
- ord-df1be2fa6fdf4514b1cfc191a598f30a
- Source dataset
- uspto-grants-1990_01
- Patent number
- US04895860
Reaction notes
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