tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate → N-[[2'-(t-butoxycarbonyl)biphenyl-4-yl]methyl]phthalimide
Reaction equation
[C:1]([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20]Br)=[CH:16][CH:15]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]1(=[O:32])[NH:26][C:25](=[O:27])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.[K]>CN(C=O)C>[C:1]([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:26]3[C:22](=[O:32])[C:23]4[C:24](=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:25]3=[O:27])=[CH:16][CH:15]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
4′-Bromomethylbiphenyl-2-carboxylic acid t-butyl ester (4.0 g, 11.5 mmol) and potassium phthalimide were combined and dissolved in DMF (30 mL), and the mixture was heated at 50° C. for two days. The mixture was then cooled to room temperature and the reaction quenched with water (30 mL). The mixture was then extracted with EtOAc, and washed with a 10% aqueous lithium chloride solution. The organic layer was dried over MgSO4, filtered and concentrated to obtain intermediate (22a) (4.8 g). MS m/z: [M+H+] calcd for C26H23NO4, 414.5. found 414.3.
Workup
- temperatureThe mixture was then cooled to room temperature
- customthe reaction quenched with water (30 mL)
- extractionThe mixture was then extracted with EtOAc
- washwashed with a 10% aqueous lithium chloride solution
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bff4c2f1c9c34ca99fbc502cd199d2bc
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273008B2
Reaction notes
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