Acrylic Acid → 3-(4-Bromo-3-methylphenylthio)propionic acid
Reaction equation
[C:1]1([CH3:8])[CH:6]=[CH:5][CH:4]=[C:3]([SH:7])[CH:2]=1.[C:9]([OH:13])(=[O:12])[CH:10]=[CH2:11].[Br:14]Br.S.[Na]>C(O)(=O)C.C(N(CC)CC)C>[Br:14][C:6]1[CH:5]=[CH:4][C:3]([S:7][CH2:11][CH2:10][C:9]([OH:13])=[O:12])=[CH:2][C:1]=1[CH3:8]Participants
Conditions
- Temperature
- 50 °C
Procedure
A one-liter, three-necked flask was charged with 50 g (0.4 mol) of m-toluenethiol, 29 g (0.4 mol) of acrylic acid and 1.0 ml of triethylamine, and the mixture was allowed to react at 150° C. for 1 hour. After the reaction mixture was allowed to cool, 200 ml of acetic acid was added to the reaction mixture, and the mixture was heated up to 50° C. to form a complete solution. Then, 21 ml of bromine was gradually added over 30 minutes, and the mixture was further allowed to react at 50° to 60° C. for 1 hour. After the reaction was completed, the reaction mixture was poured into 1.5 liters of a 1% sodium hydrogensulfide aqueous solution, and the formed solid was recovered by filtration and dried to give 110 g of 3-(4-bromo-3-methylphenylthio)-propionic acid as a crude product.
Workup
- customto react at 150° C. for 1 hour
- temperatureto cool
- customto form a complete solution
- customto react at 50° to 60° C. for 1 hour
- filtrationthe formed solid was recovered by filtration
- customdried
Sources & evidence
- ORD record
- ord-761e06946ac24701bb6a8ba510789f19
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05587484
Reaction notes
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