Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[CH:9])[CH:3]=1.C(Br)C.[Mg].[CH3:14][Si:15](Cl)([CH3:17])[CH3:16].[NH4+].[Cl-]>O1CCCC1>[CH3:14][Si:15]([C:9]#[C:8][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=1)([CH3:17])[CH3:16]Participants
6
Conditions
- Temperature
- 25 °C
Procedure
Under an inert atmosphere, 9.5 g of the compound of Step A were introduced into 100 g of tetrahydrofuran, and at 25° C.±3° C., over 15 minutes, 69 ml of a 0.8M solution of magnesium ethyl bromide were added, with stirring for 15 minutes at 25° C. Then, over 2 minutes and without cooling, 8 ml of trimethylsilyl chloride were added with stirring for 30 minutes at 25° C. The reaction mixture was poured into a 2M aqueous solution of NH4Cl and was extracted with ether, dried, filtered, and the filtrate was concentrated to dryness by distilling under reduced pressure then rectified to obtain 12.1 g of 3-(trimethylsilylethynyl)bromobenzene with a boiling point at 0.05 mm/Hg=78° to 84° C.
Workup
- waitThen, over 2 minutes
- temperaturewithout cooling
- stirringwith stirring for 30 minutes at 25° C
- extractionwas extracted with ether
- customdried
- filtrationfiltered
- concentrationthe filtrate was concentrated to dryness
- distillationby distilling under reduced pressure
Sources & evidence
- ORD record
- ord-b45ad6403f1a42f39b80f269ce0cdad9
- Source dataset
- uspto-grants-1990_03
- Patent number
- US04912097
Linked notes
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