Water → HCID 22000390, compound
Reaction equation
[CH2:1]1[CH2:8][C:7]2[CH:9]=[CH:10][C:11]([F:13])=[CH:12][C:6]=2[C:4](=[O:5])[CH2:3][CH2:2]1.[Br:14]Br.O>C(O)(=O)C>[Br:14][CH:3]1[CH2:2][CH2:1][CH2:8][C:7]2[CH:9]=[CH:10][C:11]([F:13])=[CH:12][C:6]=2[C:4]1=[O:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 8-fluoro-1-benzosuberone (20.00 g, 112.2 mmol) in glacial acetic acid (125 ml) was added bromine (5.8 ml, 112.6 mmol) dropwise. Once the addition was complete, the solution was poured into water (400 ml) and extracted with EtOAc (500 ml). The extract was separated and washed with water (500 ml). The organic layer was dried over MgSO4, filtered and evaporated to yield 100% (28.9 g) of the desired product as a viscous oil: 1H-NMR (CDCl3) δ 2.00 (2H, m), 2.33 (2H, m), 2.84 (1H, m), 3.00 (1H, m), 4.83 (1H, m), 7.13 (2H, m), 7.29 (1H, dd).