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1-(5-BROMO-THIOPHEN-2-YL)-PROPAN-1-ONE synthesis

3synthesis methods
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Yield:32412-39-8 95%

Reaction Conditions:

Stage #1: propionyl chloridewith aluminum (III) chloride in 1,2-dichloro-ethane at 0; for 0.333333 h;
Stage #2: 2-bromothiophene in 1,2-dichloro-ethane at 0 - 20;

Steps:

Synthesis 1-(5-bromothiophen-2-yl)propan-1-one (227)

To a stirred solution of AlCl3 (29.44 g, 221 mmol) in EDC (300 mL) at 0C, propionyl chloride (17.02 g, 184 mmol) was added and reaction mixture was stirred for 20 min at 0C. To this solution, compound 231 (30 g, 184 mmol) was added and further stirred at room temperature for overnight. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water and extracted with DCM. The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to afford the title compound 227 (38.20 g, 95%) as brown coloured solid; TLC: 20% EtOAc/ hexane (Rf: 0.4); 1H NMR (400 MHz, DMSO-d6): δ 7.79 (d, J=4.4 Hz, 1H), 7.38 (d, J=4.0 Hz, 1H), 2.97-2.92 (m, 2H), 1.07 (t, J=7.2 Hz, 3H); LCMS Calculated for C7H7BrOS: 217.94; Observed: 220.80 (M + 2)+.

References:

WO2018/160878,2018,A1 Location in patent:Page/Page column 387

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