Sodium Acetate → 8-bromo-2-methoxy-6H-dibenzo[c,h]chromene
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:21]=1)[CH2:7][O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.C([O-])(=O)C.[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10]3[C:9](=[C:18]4[CH:17]=[CH:16][C:15]([O:19][CH3:20])=[CH:14][C:13]4=[CH:12][CH:11]=3)[O:8][CH2:7][C:6]=2[CH:21]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
A mixture of 1-(5-bromo-2-iodobenzyloxy)-6-methoxynaphthalene (5.0 g, 10.7 mmol) and sodium acetate (2.64 g, 32.1 mmol) in dimethylformamide (100 mL) was degassed with a stream of argon for 15 minutes. PdCl2(PPh3)2 was added and the reaction was heated to 110° C. After 16 hours the reaction was diluted with ethyl acetate, washed with water and brine, dried (Na2SO4) and concentrated. The resulting residue was purified by flash column chromatography to yield 8-bromo-2-methoxy-6H-dibenzo[c,h]chromene (1.29 g, 35%).