1-[3-(3,4-Dichloro-benzyloxy)-phenyl]-ethanone → 2-Bromo-1-[3-(3,4-dichloro-benzyloxy)-phenyl]-ethanone
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:5][O:6][C:7]1[CH:8]=[C:9]([C:13](=[O:15])[CH3:14])[CH:10]=[CH:11][CH:12]=1.C1CNC(=O)C1.[Br:26][Br-]Br>CO.C(Cl)Cl>[Br:26][CH2:14][C:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][CH2:5][C:4]2[CH:16]=[CH:17][C:18]([Cl:19])=[C:2]([Cl:1])[CH:3]=2)[CH:8]=1)=[O:15]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
1-[3-(3,4-Dichloro-benzyloxy)-phenyl]-ethanone (30 g) was dissolved in MeOH:DCM (2:1, 300 mL) and pyrolidone hydrotribromide (75 g) was added portion wise and stirred at room temperature for 3 hours. After completion of the reaction, the mixture was concentrated in vacuo and poured into saturated sodium bicarbonate solution (200 mL) and extracted with ethyl acetate (2×200 mL). The organic extracts were combined and washed with brine and concentrated in vacuo. Then this residue was dissolved in DCM (75 mL) and product was precipitated by slow addition of methanol (75 mL), filtered and dried in vacuum (29 g). 1H NMR (400 MHz, CDCl3): 7.62-7.54 (m, 3H), 7.47 (d, 1H), 7.42 (t, 1H), 7.25-7.30 (m, 1H), 7.18-7.23 (m, 1H), 5.07 (s, 2H), 4.44 (s, 2H).
Workup
- customAfter completion of the reaction
- concentrationthe mixture was concentrated in vacuo
- additionpoured into saturated sodium bicarbonate solution (200 mL)
- extractionextracted with ethyl acetate (2×200 mL)
- washwashed with brine
- concentrationconcentrated in vacuo
- dissolutionThen this residue was dissolved in DCM (75 mL)
- customproduct was precipitated by slow addition of methanol (75 mL)
- filtrationfiltered
- customdried in vacuum (29 g)
Sources & evidence
- ORD record
- ord-8c4bb54907574b6a8a5f8e1767ec727e
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383644B2
Reaction notes
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