Resorcinol → HCID 20532528, compound
Reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].Br[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1.Cl.CN(C)CC(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O.C(OCC)(=O)C.[Cu]I>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([O:2][C:1]2[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][CH:8]=2)=[CH:11][CH:12]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
A suspension of resorcinol (12.58 g, 114.2 mmol), 4-bromochlorobenzene (10.94 g, 57.14 mmol), dimethylglycine HCl (2.39 g, 17.1 mmol), and cesium carbonate (37.2 g, 114 mmol) in DMA (80 mL) was treated with CuI (1.09 g, 5.71 mmol) and heated at 90° C. for 16 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (500 mL) and extracted with 1 N NaOH (400 mL), and brine (200 mL). The organic layer was dried (MgSO4) and concentrated. The residue was purified (FCC) to give the title compound as a yellow oil (7.6 g, 60%). MS (ESI+): calcd. for C12H9ClNO2, 220.03. m/z found, 221.1 (M+H)+. 1H NMR (d6-DMSO): 9.63 (s, 1H), 7.43 (d, J=8.9 Hz, 2H), 7.17 (t, J=8.1 Hz, 1H), 7.03 (d, J=8.9 Hz, 2H), 6.58-6.54 (m, 1H), 6.46-6.41 (m, 1H), 6.38 (t, J=2.3 Hz, 1H).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- extractionextracted with 1 N NaOH (400 mL), and brine (200 mL)
- dry with materialThe organic layer was dried (MgSO4)
- concentrationconcentrated
- customThe residue was purified (FCC)
Sources & evidence
- ORD record
- ord-413772c949054434ad4cac9842e42875
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901111B2
Reaction notes
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