Hydrochloric Acid → 1-(6-Bromonaphthalen-2-yl)ethanone
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12](N(OC)C)=[O:13])[CH:6]=[CH:5]2.[CH3:18][Mg]Br.Cl>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12](=[O:13])[CH3:18])[CH:6]=[CH:5]2Participants
Conditions
- Temperature
- 12.5 °C
Procedure
6-bromo-N-methoxy-N-methyl-2-naphthamide (82.9 g, 282 mmol, 1 equiv.) was dissolved in tetrahydrofurane (600 mL) in a 4-neck flask under nitrogen. The reaction mixture was cooled in an ice bath and methyl magnesium bromide (3.2 M in methyl-tetrahydrofurane, 197 mL, 2.2 equiv.) was added drop wise during 1 hour, while maintaining the temperature of the reaction mixture between 10-15° C. The reaction mixture was stirred 30 minutes further in an ice bath. Aqueous hydrochloric acid (2 M, 100 mL) was then carefully added drop wise while cooling on an ice bath. The organic solvent was evaporated and the precipitated product extracted with dichloromethane (500 mL). The solution was dried over sodium sulphate, filtered and concentrated. The solid residue was dried in vacuum at 40° C. yielding 1-(6-bromonaphthalen-2-yl)-ethanone (70.6 g, 99%).
Workup
- temperatureThe reaction mixture was cooled in an ice bath
- temperaturecarefully added drop wise while cooling on an ice bath
- customThe organic solvent was evaporated
- extractionthe precipitated product extracted with dichloromethane (500 mL)
- dry with materialThe solution was dried over sodium sulphate
- filtrationfiltered
- concentrationconcentrated
- customThe solid residue was dried in vacuum at 40° C.
Sources & evidence
- ORD record
- ord-ac829fdf154e4a9aaa5812f622a5b372
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09433609B2
Reaction notes
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