Hydrochloric Acid → HCID 21915324, compound

HRID 1787521Notes

Reaction equation

[Br:1][C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1.Cl.O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:13]([C:12]1[CH:16]=[CH:17][C:9]([O:8][CH3:7])=[CH:10][CH:11]=1)=[O:14]

Participants

Conditions

Temperature: 2.5 °C

Procedure

Treat a stirred, chilled (0° C.) solution of 3-bromothiophene (20 g, 0.123 mol) and dichloromethane (150 mL) with titanium tetrachloride in dichloromethane (184 mL, 1.0M) at such a rate as to maintain the temperature below 5° C. Add dropwise a solution of 4-methoxybenzoyl chloride (20.9 g, 0.123 mol) and dichloromethane (75 mL) at such a rate as to maintain the temperature below 5° C. Stir one hour at 0-5° C., then quench the reaction by addition of ice (100 mL) and 6N hydrochloric acid at such a rate that the internal temperature remains at or below 10° C. Add more water (100 mL), separate the organic phase, wash with water, dry (Na2SO4), filter and evaporate to an oil which solidifies. Recrystallize the solid from ether to afford the title compound as off-white crystals (19.7 g, 54%).

Workup

additionTreat a stirred
temperatureto maintain the temperature below 5° C
temperatureto maintain the temperature below 5° C
customquench
customthe reaction
custombelow 10° C
customseparate the organic phase
washwash with water
dry with materialdry (Na2SO4)
filtrationfilter
customevaporate to an oil which
customRecrystallize the solid from ether

Sources & evidence

ORD record: ord-beb22e32c16c4231ae4fc22a94c0ecf0
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511046B2

Reaction notes

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