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23rd October 2013 @ 04:56

To MNR 99-3 (2.10 g, 12.3 mmol, 1.0 equiv.) in THF (120 mL) at -78 C was added n-BuLi (7.38 mL, 18.5 mmol, 1.5 equiv.) dropwise and the reaction mixture stirred at -78 C for 30 minutes. Bromine (1.26 mL, 24.6 mmol, 2.0 equiv.) was added dropwise and the reaction mixture warmed to rt and stirred for 1 h. Some SM but also product on TLC plate. The reaction mixture was diluted with an aqueous solution of sodium thiosulfate (150 mL) and extracted into ethyl acetate (3 x 100 mL). The combined organic extracts were dried (MgSO4), concentrated under reduced pressure and the residue purified by flash column chromatography (7:1 hexanes:ethyl acetate) to give the desired product as a pale yellow solid (1.73 g, 6.93 mmol, 56% yield) and a second fraction containing SM.

Data:

Crude NMR

AEW 99-1.cdxml
AEW 99-1 crude proton.pdf

After column

AEW 99-1 first spot.pdf
AEW 99-1 first spot.mnova
AEW 99-1 col frac A.zip

Hazard and Risk Assessment:

See Bromination of chlorothienopyrimidine (AT-5-1)

InChi:

InChI=1S/C6H3ClN2S/c7-6-5-4(1-2-10-5)8-3-9-6/h1-3H

to

InChI=1S/C6H2BrClN2S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H

 

See Also:

Bromination of chlorothienopyrimidine (AT-5-1)

Bromination of chlorothienopyrimidine (AT-5-2)

Bromination of chlorothienopyrimidine (AT-5-3)

Bromination of chlorothienopyrimidine (AT-5-5)

Bromination of chlorothienopyrimidine (AT-5-6)

Linked Entries
Attached Files
AEW 99-1.png
AEW 99-1.cdxml
AEW 99-1 crude proton.pdf
AEW 99-1 crude proton.mnova
AEW 99-1 first spot.pdf
AEW 99-1 first spot.mnova
AEW 99-1 col frac A.zip