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10th July 2012 @ 00:03
Starting material consumed, potential double sulfonation.

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Chlorosulfonation of aryl pyrrole PMY 1-6 using chlorosulfonic acid.

PMY54-1.png

Reaction Start Time: 9.50 10/07/12
Solid PMY 1-6 (250 mg, 1.3 mmol, 1 equiv.) was mixed under an inert atmosphere at room temperature. Chlorosulfonic acid (0.5 mL, 7.5 mmol, 5.7 equiv.) was added dropwise. Slight exotherm. Reaction is a brown solution. TLC (mini work-up: a drop added to water, Et2 layer TLC'd) after <5 mins, SM still present. After 2 hours, SM still present by TLC [hydrolysis product could remain in aqueous layer of mini w/up, so product may not show on TLC]. 12.00 Heated to 60 °C. 1.50, SM consumed by TLC. reaction cooled. Thick red oily reaction mixture was transferred carefully into ice/DCM (20 mL of both) and stirred until the ice had melted. Layers separated and the the aqueous extracted with DCM (2 × 10 mL). The organic extracts were washed with brine then dried (MgSO4) and concentrated under reduced pressure to a brown solid. 1H NMR shows a single methyl (still symmetriacal compound), broad aromatic region. No obvious pyrrole-4,3-H environment.

TLC (10% EtOAc/hexane) visualised with UV and vanillin:
TLC <5 min
TLC 2 hours at 60 celcius


NMR:
1H NMR crude


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Scheme
Risk Assessment
TLC <5 min
TLC <5 min
TLC 2 hours at 60 celcius
1H NMR crude