Sodium Carbonate → 7-Bromo-4-(2,4-dichlorophenyl)coumarin
Reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](OS(C(F)(F)F)(=O)=O)=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:25]3[CH:24]=[CH:23][C:22]([Cl:21])=[CH:27][C:26]=3[Cl:28])=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
To a solution of the triflate from Step 1 (712 mg, 1.91 mmol) in 15 ml THF was added 2,4-dichlorophenyl boronic acid (400 mg, 2.10 mmol), (Ph3P)4Pd (110 mg, 0.095 mmol) and aqueous Na2CO3 (1.91 mL, 3.82 mmol). The mixture was heated at 70° C. for 2 h, cooled and partitioned between aqueous NH4Cl and EtOAc (50 mL each). The layers were separated and the aqueous phase was extracted with EtOAc (3×25 mL). The combined organic layers were dried over anhydrous MgSO4. The solvent was evaporated and the residue chromatographed on silica gel (hexane: EtOAc 9:1) to give 480 mg (68%) of the title compound.
Workup
- temperaturecooled
- custompartitioned between aqueous NH4Cl and EtOAc (50 mL each)
- customThe layers were separated
- extractionthe aqueous phase was extracted with EtOAc (3×25 mL)
- dry with materialThe combined organic layers were dried over anhydrous MgSO4
- customThe solvent was evaporated
- customthe residue chromatographed on silica gel (hexane: EtOAc 9:1)
Sources & evidence
- ORD record
- ord-276cd28d0c444b5ea0487005c9d99a11
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05552437
Reaction notes
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