Sodium Carbonate → Methyl 4-bromo-5-(2,4-dichlorophenyl)-3-methoxythio-phene-2-carboxylate
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].[Br:18][C:19]1[C:20]([O:29][CH3:30])=[C:21]([C:25]([O:27][CH3:28])=[O:26])[S:22][C:23]=1Br>C1(C)C=CC=CC=1>[Br:18][C:19]1[C:20]([O:29][CH3:30])=[C:21]([C:25]([O:27][CH3:28])=[O:26])[S:22][C:23]=1[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
16.60 g of (2,4-dichlorophenyl)boronic acid and then, dropwise, 87 ml of a 2M solution of Na2CO3 are added to a solution of 28.70 g of the compound of step A) in 110 ml of toluene. Argon is sparged into the reaction mixture for 30 minutes, 5.03 g of tetrakis are then added and the mixture is heated at 110° C. for 18 hours. After cooling to AT, 80 ml of distilled water are added to the reaction mixture, extraction is carried out with 80 ml of EtOAc, drying is carried out over Na2SO4 and the solvent is evaporated off under vacuum. The reaction crude is purified by silica gel chromatography, elution being carried out with heptane and then with a heptane/EtOAc mixture (85/15; v/v). 16.21 g of the expected compound are obtained.
Workup
- customArgon is sparged into the reaction mixture for 30 minutes
- addition5.03 g of tetrakis are then added
- temperatureAfter cooling to AT, 80 ml of distilled water
- additionare added to the reaction mixture, extraction
- customdrying
- customthe solvent is evaporated off under vacuum
- customThe reaction crude
- customis purified by silica gel chromatography, elution
Sources & evidence
- ORD record
- ord-ba9c01f3100049a6899c8726b0ce7e2d
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08486971B2
Reaction notes
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